Category: iodides-buliding-blocks

N,N-Diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: A Novel, Exceptionally Selective, Potent δ Opioid Receptor Agonist with Oral Bioavailability and Its Analogues was written by Wei, Zhong-Yong;Brown, William;Takasaki, Bryan;Plobeck, Niklas;Delorme, Daniel;Zhou, Fei;Yang, Hua;Jones, Paul;Gawell, Lars;Gagnon, Helene;Schmidt, Ralf;Yue, Shi-Yi;Walpole, Chris;Payza, Kemal;St-Onge, Stephane;Labarre, Maryse;Godbout, Claude;Jakob, Andrea;Butterworth, Joanne;Kamassah, Augustus;Morin, Pierre-Emmanuel;Projean, Denis;Ducharme, Julie;Roberts, Edward. And the article was included in Journal of Medicinal Chemistry in 2000.Category: iodides-buliding-blocks This article mentions the following:

The design, synthesis, and pharmacol. evaluation of a novel class of δ opioid receptor agonists, N,N-diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide (I) and its analogs, are described. These compounds, formally derived from SNC-80 by replacing the piperazine ring with a piperidine ring containing an exocyclic carbon carbon double bond, were found to bind with high affinity and exhibit excellent selectivity for the δ opioid receptor as full agonists. I, the simplest structure in the class, exhibited an IC₅₀ = 0.87 nM for the δ opioid receptors and extremely high selectivity over the μ receptors (μ/δ = 4370) and the κ receptors (κ/δ = 8590). Rat liver microsome studies on a selected number of compounds show these olefinic piperidine compounds to be considerably more stable than SNC-80. This novel series of compounds appear to interact with δ opioid receptors in a similar way to SNC-80 since they demonstrate similar SAR. Two general approaches have been established for the synthesis of these compounds, based on dehydration of benzhydryl alcs. and Suzuki coupling reactions of vinyl bromide. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Category: iodides-buliding-blocks).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Total Synthesis of Isohericenone J via a Stille Coupling Reaction was written by Cao, Wei;Chen, Ping;Tang, Yu. And the article was included in Journal of Natural Products in 2020.Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate This article mentions the following:

The first total synthesis of isohericenone J is reported. Key features of this synthetic strategy are a Friedel-Crafts reaction to construct the isobenzofuranone unit and a Pd-catalyzed Stille coupling reaction for the formation of the C5-C1′ bond, generating the natural product, as well as one of its isomers, in 6.0% overall yield in eight steps. This strategy provides a foundation for the synthesis of challenging isobenzofuranone and isoindolinone-type derivatives In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Recommanded Product: Methyl 3,5-dihydroxy-4-iodobenzoate

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A Polar Substituent-Containing Acylation Agent for the Radioiodination of Internalizing Monoclonal Antibodies: N-Succinimidyl 4-Guanidinomethyl-3-[¹³¹I]iodobenzoate ([¹³¹I]SGMIB) was written by Vaidyanathan, Ganesan;Affleck, Donna J.;Li, Jean;Welsh, Phil;Zalutsky, Michael R.. And the article was included in Bioconjugate Chemistry in 2001.Application In Synthesis of 5-Iodonicotinic acid This article mentions the following:

The objective of this study was to develop an acylation agent for the radioiodination of monoclonal antibodies that would maximize retention of the label in tumor cells following receptor- or antigen-mediated internalization. The strategy taken was to add a polar substituent to the labeled aromatic ring to impede transport of labeled catabolites across lysosomal and cell membranes after antibody degradation Preparation of unlabeled N-succinimidyl 4-guanidinomethyl-3-iodobenzoate (SGMIB) was achieved in six steps from 3-iodo-4-methylbenzoic acid. Preparation of 4-guanidinomethyl-3-[¹³¹I]iodobenzoic acid from the silicon precursor, 4-(N¹,N²-bis-tert-butyloxycarbonyl)guanidinomethyl-3-trimethylsilylbenzoic acid proceeded in less than 5% radiochem. yield. A more successful approach was to prepare [¹³¹I]SGMIB directly from the tin precursor, N-succinimidyl 4-(N¹,N²-bis-tert-butyloxycarbonyl)guanidinomethyl-3-trimethylstannylbenzoate, which was achieved in 60-65% radiochem. yield. A rapidly internalizing anti-epidermal growth factor receptor variant III antibody L8A4 was labeled using [¹³¹I]SGMIB in 65% conjugation efficiency and with preservation of immunoreactivity. Paired-label in vitro internalization assays demonstrated that the amount of radioactivity retained in cells after internalization for L8A4 labeled with [¹³¹I]SGMIB was 3-4-fold higher than that for L8A4 labeled with ¹²⁵I using either Iodogen or [¹²⁵I]SIPC. Catabolite assays documented that the increased retention of radioiodine in tumor cells for antibody labeled using [¹³¹I]SGMIB was due to pos. charged, low mol. weight species. These results suggest that [¹³¹I]SGMIB warrants further evaluation as a reagent for labeling internalizing antibodies. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Application In Synthesis of 5-Iodonicotinic acid).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Application In Synthesis of 5-Iodonicotinic acid

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source was written by Li, Junxuan;Zhou, Jinlei;Wang, Yumei;Yu, Yue;Liu, Qiang;Yang, Tilong;Chen, Huoji;Cao, Hua. And the article was included in Science China: Chemistry in 2022.Electric Literature of C7H6FIO This article mentions the following:

Pd-catalyzed carbonylation, as an efficient synthetic approach for the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, authors show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcs. and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcs. are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermol. fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Electric Literature of C7H6FIO).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Electric Literature of C7H6FIO

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of Enantiopure Bicyclic α,α-Disubstituted Spirolactams via Asymmetric Birch Reductive Alkylation was written by Gueret, Stephanie M.;O’Connor, Patrick D.;Brimble, Margaret A.. And the article was included in Organic Letters in 2009.Name: 1-Chloro-4-iodobutane This article mentions the following:

The synthesis of enantiopure bicyclic α,α-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramol. cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones, e.g. I. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Name: 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Name: 1-Chloro-4-iodobutane

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Accessing 2-Arylbenzofurans by Cu^I₂(pip)₂-Catalyzed Tandem Coupling/Cyclization Reaction: Mechanistic Studies and Application to the Synthesis of Stemofuran A and Moracin M was written by Chen, Hong-Bin;Qin, Dan-Dan;Chen, Wei;Tang, Xiao;Yu, Wen;Wu, An-An;Liao, Yi. And the article was included in Asian Journal of Organic Chemistry in 2016.Product Details of 207115-22-8 This article mentions the following:

An asym. dinuclear copper(I) complex, Cu^I2(pip)₂ (pip = (2-picolyliminomethyl)pyrrole anion), was utilized to catalyze the tandem coupling/cyclization reaction of o-iodophenols and terminal alkynes, which led to the formation of valuable 2-arylbenzofurans I (R¹ = Ph, 4-EtC₆H₄, 1-naphthyl, etc.; R² = H, 4-MeO, 4-t-Bu, 4-Ph, 4-F, 4-Br) in good yields. DFT calculations showed that the two proximate copper atoms play cooperative roles throughout the catalytic cycle. Using this catalytic protocol, bioactive natural products stemofuran A and moracin M were concisely synthesized. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Product Details of 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Product Details of 207115-22-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The synthesis of substituted 9-oxoacridan-4-carboxylic acids; part 3. The reaction of methyl anthranilates with diphenyliodonium-2-carboxylates was written by Rewcastle, Gordon W.;Denny, William A.. And the article was included in Synthesis in 1985.SDS of cas: 13420-63-8 This article mentions the following:

Twenty-two 9-oxoacridan-4-carboxylic acids I (R = H, 1-Me, 1-OMe, 1-Cl, 1-NO₂, 1-CO₂H, 2-Me, 3-Me, etc., R¹ = H, R = H, R¹ = 6-NH₂, 6-Cl, 6-NO₂, 7-NO₂, 8-Me, 8-Cl) were prepared by cyclization of anilinobenzoates II followed by saponification II were prepared by treating diphenyliodonium-2-carboxylates III with Me anthranilates IV. In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8SDS of cas: 13420-63-8).

2-Chloro-6-iodobenzoic acid (cas: 13420-63-8) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.SDS of cas: 13420-63-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

adj-Dicarbaporphyrinoid Systems: Synthesis, Spectroscopic Characterization, and Reactivity of 23-Carbabenziporphyrins was written by Jain, Pankaj;AbuSalim, Deyaa I.;Lash, Timothy D.. And the article was included in Journal of Organic Chemistry in 2019.Safety of 3-Iodo-4-methoxybenzaldehyde This article mentions the following:

A new family of adj-dicarbaporphyrinoids has been prepared using the “2 + 2” MacDonald methodol. Dibutylboron triflate catalyzed condensation of 3-iodo-4-methoxybenzaldehyde with an indene enamine afforded an iodofulvene aldehyde; and a related dimethoxyfulvene was similarly prepared in two steps from 2,4-dimethoxybenzaldehyde. Following protection as the corresponding di-Me acetals, the iodofulvenes were metalated with Bu₃MgLi at -100 °C and reacted with DMF to give the required fulvene dialdehyde intermediates. Acid-catalyzed condensation with three different dipyrrylmethanes afforded a series of benzo-23-carbabenziporphyrins I (R = Et, Me, CH₂CH₂CO₂Me, X = H; R = Et, Me, CH₂CH₂CO₂Me, X = OMe) in 52-70% yields. The proton NMR spectra for these adj-dicarbaporphyrinoids indicate that these macrocycles are slightly diatropic. Monoprotonation afforded cationic species with slightly larger aromatic ring currents, and under strongly acidic conditions, C-protonated dications were generated with substantial diatropic properties. The aromatic character of these structures was supported by nucleus-independent chem. shifts and anisotropy of induced c.d. calculations The computational results indicate that the dications favor 23-atom 22π electron delocalization pathways. The benzo-23-carbabenziporphyrins were selectively oxidized with silver(I) acetate in dichloromethane-methanol to give stable nonaromatic structures with two addnl. methoxy substituents connected to sp³ hybridized bridging carbons. The intriguing reactivity and unique spectroscopic properties of benzo-23-carbabenziporphyrins make these novel structures promising candidates for further investigations. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Safety of 3-Iodo-4-methoxybenzaldehyde).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Safety of 3-Iodo-4-methoxybenzaldehyde

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Palladium-Catalyzed Regioselective Carbonylative Coupling/Amination of Aryl Iodides with Unactivated Alkenes: Efficient Synthesis of β-Aminoketones was written by Peng, Jin-Bao;Wu, Fu-Peng;Li, Da;Geng, Hui-Qing;Qi, Xinxin;Ying, Jun;Wu, Xiao-Feng. And the article was included in ACS Catalysis in 2019.Recommanded Product: 5460-32-2 This article mentions the following:

The carbonylative coupling of aryl halides with unactivated alkenes remains a challenge, because of the low reactivity of acyl-palladium intermediate to the olefins. A palladium-catalyzed carbonylative coupling/amination of aryl iodides with unactivated alkenes for the synthesis of β-aminoketone derivatives was developed. With the assistance of a directing group (8-aminoquinoline, AQ), the coordination of the olefin to acyl-palladium complex can be enhanced, thereby promoting the acylpalladation across the C:C double bonds. A broad range of β-aminoketone derivatives were prepared in moderate to excellent yields with complete regioselectivity by using 4-pentenoic and 2-vinylbenzoic amide derivatives as the starting materials. This methodol. involves the formation of two C-C bonds as well as one C-N bond, and provided a method for the carbonylative difunctionalization of unactivated alkenes. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Recommanded Product: 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Recommanded Product: 5460-32-2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of new bis[heterocycles] by a one-pot Sonogashira coupling reaction was written by Deodhar, Mandar;Black, David StC;Kumar, Naresh. And the article was included in Heterocycles in 2011.Computed Properties of C8H7IO2 This article mentions the following:

Halogenated flavones, isoflavones and indoles were subjected to a one-pot Sonogashira coupling reaction and the synthesis of the target compounds was achieved in good yield. For example, iodination and Sonogashira coupling of Daidzein diacetate [7-(acetyloxy)-3-[4-(acetyloxy)phenyl]-4H-1-benzopyran-4-one] with (trimethylsilyl)acetylene thus provided 2,1-ethynediyl(methoxy-4,1-phenylene)bis[7-methoxy-4H-1-benzopyran-4-one]. The methodol. can be readily adapted to the synthesis of a wide variety of substituted bis[heterocyclic compounds]. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Computed Properties of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Computed Properties of C8H7IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com