Category: 167479-01-8

Schramm, Simon; Agnetta, Luca; Bermudez, Marcel; Gerwe, Hubert; Irmen, Matthias; Holze, Janine; Littmann, Timo; Wolber, Gerhard; Traenkle, Christian; Decker, Michael published the artcile< Novel BQCA- and TBPB-derived M1 receptor hybrid ligands: orthosteric carbachol differentially regulates partial agonism>, Safety of tert-Butyl (3-iodopropyl)carbamate, the main research area is BQCA TBPB carbachol muscarinic M1 agonist; GPCRs; allostery; dualsteric ligands; muscarinic receptors; partial agonists.

Recently, investigations of the complex mechanisms of allostery have led to a deeper understanding of G protein-coupled receptor (GPCR) activation and signaling processes. In this context, muscarinic acetylcholine receptors (mAChRs) are highly relevant due to their exemplary role in the study of allosteric modulation. In this work, we compare and discuss two sets of putatively dualsteric ligands, which were designed to connect carbachol to different types of allosteric ligands. We chose derivatives of TBPB [1-(1′-(2-tolyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one] as M1-selective putative bitopic ligands, and derivatives of benzyl quinolone carboxylic acid (BQCA) as an M1 pos. allosteric modulator, varying the distance between the allosteric and orthosteric building blocks. Luciferase protein complementation assays demonstrated that linker length must be carefully chosen to yield either agonist or antagonist behavior. These findings may help to design biased signaling and/or different extents of efficacy.

ChemMedChem published new progress about Homo sapiens. 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Safety of tert-Butyl (3-iodopropyl)carbamate.

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

Yang, Peng-Fei; Shu, Wei published the artcile< Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations>, Name: tert-Butyl (3-iodopropyl)carbamate, the main research area is amine preparation regioselective; chiral amine preparation regioselective enantioselective; alkenyl amine alkyl halide hydroalkylation metal catalyst; Amines; Chain Walking; Cobalt Catalysis; Hydroalkylations; Regiodivergent Reactions.

Herein, a catalyst-controlled synthesis of α-branched e.g., N-(1-phenylpentan-3-yl)benzamide, β-branched e.g., N-(2-methyl-4-phenylbutyl)benzamide and linear aliphatic amines e.g., N-(5-phenylpentyl)benzamide from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines e.g., N-(prop-2-en-1-yl)benzamide with alkyl halides RX (R = butan-2-yl, Bn, 2-phenylethyl, 2-(1,3-dioxolan-2-yl)ethyl, etc.; X = I, Br) is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chem. to catalytically repurpose three types of alkyl amines under mild conditions.

Angewandte Chemie, International Edition published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Name: tert-Butyl (3-iodopropyl)carbamate.

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

Yang, Tao; Chen, Xianxiao; Rao, Weidong; Koh, Ming Joo published the artcile< Broadly Applicable Directed Catalytic Reductive Difunctionalization of Alkenyl Carbonyl Compounds>, Computed Properties of 167479-01-8, the main research area is alkenyl carbonyl reductive difunctionalization nickel catalyst.

Catalytic alkene difuntionalization is a convenient platform for introducing complexity in mols. and has wide applications in organic synthesis. Yet a compelling challenge that remains to be solved is the regioselective insertion of two highly functionalized carbon-based moieties, derived from stable and readily available organohalide electrophiles without the need for pre-synthesized organometallic reagents, across C=C bonds in unactivated alkyl-substituted alkenes. That catalytic amounts of an inexpensive Ni-based catalyst, in combination with a readily recyclable 8-aminoquinoline directing group, promotes efficient and site-selective addition of two different organohalides (iodides and bromides) across aliphatic alkenes under mild reductive conditions. Compared to previous studies, this protocol exhibits broad and complementary functional group tolerance that extends to aryl-alkylation, alkenyl-alkylation, and dialkylation transformations. The utility of the strategy is demonstrated through concise synthesis of biol. active mols. Kinetic studies and other control experiments shed further light on the mechanistic underpinnings of the multicomponent reaction.

Chem published new progress about Alkenylation. 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Computed Properties of 167479-01-8.

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

Koo, Seung Moh; Vendola, Alex J.; Momm, Sarah Noemi; Morken, James P. published the artcile< Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp3) Electrophiles: Reaction Development and Application to Targets of Interest>, Recommanded Product: tert-Butyl (3-iodopropyl)carbamate, the main research area is alkyl migration cross coupling nickel catalyst; organoboronic ester preparation cross coupling nickel catalyst; coniine indolizidine 209D preparation cross coupling nickel catalyst.

A catalytic conjunctive cross-coupling reaction was developed that allows the construction of chiral organoboronic esters from alkylboron ate complexes and alkyl iodide electrophiles. The process occurs most efficiently with a Ni/Pybox-comprised catalyst and with an acenaphthoquinone-derived boron ligand. Because of the broad functional group tolerance of this reaction, it can be a versatile tool for organic synthesis. Applications to the construction of (R)-coniine and (-)-indolizidine 209D are described.

Organic Letters published new progress about Boronic acids, esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Recommanded Product: tert-Butyl (3-iodopropyl)carbamate.

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

Dey, Purusattam; Jana, Sayan K.; Rai, Pramod; Maji, Biplab published the artcile< Dicarbofunctionalizations of an Unactivated Alkene via Photoredox/Nickel Dual Catalysis>, SDS of cas: 167479-01-8, the main research area is unactivated alkene dicarbofunctionalization photoredox nickel dual catalysis.

1,2-Dicarbofunctionalization of unactivated olefin has been reported under photoredox/nickel dual catalysis. The mildness of the visible-light-mediated reaction allows the use of various alkyl and aryl electrophiles with several sensitive functional groups. The protocol was equally applied for late-stage diversification of drugs and biol. active mols. Investigations elucidated the importance of photoredox/nickel dual catalysis and α-amino-radical-mediated halogen atom transfer and provided with the nickel complexes involved in the reaction.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, SDS of cas: 167479-01-8.

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

Wang, Jia-Wang; Li, Yan; Nie, Wan; Chang, Zhe; Yu, Zi-An; Zhao, Yi-Fan; Lu, Xi; Fu, Yao published the artcile< Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines>, Electric Literature of 167479-01-8, the main research area is enamine alkyl halide nickel reductive alkylation regioselective enantioselective diastereoselective; enecarbamate alkyl halide nickel reductive alkylation regioselective enantioselective diastereoselective; chiral aliphatic amine preparation.

A mild and general nickel-catalyzed asym. reductive hydroalkylation effectively converted to enamides and enecarbamates into drug-like α-branched chiral amines was reported. This reaction involved the regio- and stereoselective hydrometallation of an enamide or enecarbamate to generated a catalytic amount of enantioenriched alkylnickel intermediate, followed by C-C bond formation via alkyl electrophiles.

Nature Communications published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Electric Literature of 167479-01-8.

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

Clark, Jennifer M.; Salgado-Polo, Fernando; Macdonald, Simon J. F.; Barrett, Tim N.; Perrakis, Anastassis; Jamieson, Craig published the artcile< Structure-Based Design of a Novel Class of Autotaxin Inhibitors Based on Endogenous Allosteric Modulators>, Electric Literature of 167479-01-8, the main research area is structure based design steroid autotaxin inhibitors endogenous allosteric modulator.

Autotaxin (ATX) facilitates the hydrolysis of lysophosphatidylcholine to lysophosphatidic acid (LPA), a bioactive phospholipid, which facilitates a diverse range of cellular effects in multiple tissue types. Abnormal LPA expression can lead to the progression of diseases such as cancer and fibrosis. Previously, we identified a potent ATX steroid-derived hybrid (partially orthosteric and allosteric) inhibitor which did not form interactions with the catalytic site. Herein, we describe the design, synthesis, and biol. evaluation of a focused library of novel steroid-derived analogs targeting the bimetallic catalytic site, representing an entirely unique class of ATX inhibitors of type V designation, which demonstrate significant pathway-relevant biochem. and phenotypic biol. effects. The current compounds modulated LPA-mediated ATX allostery and achieved indirect blockage of LPA1 internalization, in line with the observed reduction in downstream signaling cascades and chemotaxis induction. These novel type V ATX inhibitors represent a promising tool to inactivate the ATX-LPA signaling axis.

Journal of Medicinal Chemistry published new progress about Allosteric modulators. 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Electric Literature of 167479-01-8.

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

Yang, Peng-Fei; Zhu, Lei; Liang, Jian-Xing; Zhao, Han-Tong; Zhang, Jian-Xin; Zeng, Xian-Wang; Ouyang, Qin; Shu, Wei published the artcile< Regio- and Enantioselective Hydroalkylations of Unactivated Olefins Enabled by Nickel Catalysis: Reaction Development and Mechanistic Insights>, SDS of cas: 167479-01-8, the main research area is mechanism hydroalkylation olefin alkyl halide regioselective enantioselective nickel catalyst; alkene alkyl halide nickel catalyst enantioselective regioselective hydroalkylation; alkyl amide preparation.

Direct construction of fully alkyl-substituted tertiary chiral centers remote to activating groups is highly challenging and desirable. Herein, a Ni-catalyzed enantioselective hydroalkylation of unactivated alkenes with unactivated alkyl halides at room temperature is reported, providing a general and practical access to fully alkyl-substituted tertiary stereogenic carbon centers not adjacent to activating groups. This reaction undergoes regio- and stereoselective hydrometalation of unactivated alkenes with a nontrivial Markovnikov selectivity, followed by cross-coupling with unactivated alkyl electrophiles to access trialkyl tertiary saturated stereogenic centers not adjacent to activating groups. The mild and robust conditions enable the use of terminal and internal unactivated alkenes and unactivated primary and secondary alkyl, benzyl and propargyl halides to construct diverse trialkyl tertiary stereogenic carbon centers with broad functional group tolerance. Moreover, exptl. investigations support the reaction undergoing irreversible and stereoselective hydrometalation of alkenes. D. functional theory calculations provide further insights into the reaction mechanism, suggesting a stereoselective migration insertion of alkenes with Ni(II)-H species. Finally, the origin of the regio- and enantioselectivities was also investigated.

ACS Catalysis published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, SDS of cas: 167479-01-8.

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

Some common heterocyclic compound, 167479-01-8, name is tert-Butyl (3-iodopropyl)carbamate, molecular formula is C8H16INO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of tert-Butyl (3-iodopropyl)carbamate

Step B: Methyl 2-(5-(bis(tert-butoxycarbonyl amino -4-phenylpyrimidin-2-yl -5-((tert- butoxycarbonyl)amino)pentanoateTo a mixture of 2-((5-(bis-ter?-butoxycarbonyl)amino-4-phenylpyrimidin-2-yl)) acetate (300 mg, 0.676 mmol) and tert-butyl (3-iodopropyl) carbamate (231 mg, 0.812 mmol) in THF (6 mL) at 25 C was added potassium 2-methylpropan-2-olate (1.35 mL, 1.35 mmol). The resulting mixture was stirred at 25 C for 12 h then partitioned between water (30 mL) and EtOAc (30 mL x 3). The combined organic layers were dried over a2S04 and concentrated to give the title compound. MS: m/z = 601.4 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 167479-01-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 167479-01-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 167479-01-8, name is tert-Butyl (3-iodopropyl)carbamate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of an aminoalcohol (66.6 mmol) in THF (67 mL) was added di-tert-butyl dicarbonate (15.3 g, 66.6 mmol) at 50 C under an argon atmosphere. After 3 h stirring, the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography (EtOAc / hexane, 50:50) to give a N-Boc aminoalcohol. Iodine (12.5 g, 49.3 mmol) was added to a solution of N-Boc aminoalcohol (17.6 mmol), PPh3 (6.92 g, 26.3 mmol) and imidazole (1.79 g, 26.3 mmol) in CH2Cl2 (98 mL) at 0 C. The mixture was stirred at room temperature for 1 h under an argon atmosphere. The reaction mixture was quenched with saturated aqueous Na2S2O3, diluted with CH2Cl2 and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane, 10:90) to afford a N-BOC aminoalkyliodide. To a solution of NaH (60% in oil, 0.673 g, 16.8 mmol) in DMF (15.3 mL) was added dropwise a solution of N-hydroxyphthalimide (2.49 mmol) in DMF (10 mL) at 0 C under an argon atmosphere. After 15 min of stirring, a solution of the iodide (15.3 mmol) in DMF (10 mL) was added dropwise to the solution and stirred at 70 C for 12 h. After cooled to 0 C, the reaction was quenched with H2O and filtrated to afford colorless solid, which was recrystallized to give a N-alkoxyphthalimide 13a-d.

The synthetic route of tert-Butyl (3-iodopropyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fukuda, Hiroshi; Nishikawa, Keisuke; Fukunaga, Yukihiro; Okuda, Katsuhiro; Kodama, Kozue; Matsumoto, Kenji; Kano, Arihiro; Shindo, Mitsuru; Tetrahedron; vol. 72; 41; (2016); p. 6492 – 6498;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com