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497401

( R )-(+)-2-甲基-2-丙亚磺酰胺

Name: (<I> R </I>)-(+)-2-甲基-2-丙亚磺酰胺
Brand: ALDRICH

98%

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别名:

(R)-2-methyl-2-propanesulfinamide, (R)-2-methylpropane-2-sulfinamide, (R)-tert-butanesulfinamide, (R)-tert-butylsulfinamide

线性分子式:

(CH₃)₃CS(O)NH₂

CAS号:

196929-78-9

分子量:

121.20

MDL编号:

MFCD05861479

PubChem化学物质编号:

24873117

NACRES:

NA.22

检测方案

98%

旋光性

[α]20/D +4°, c = 1.0242 in chloroform stab. with amylenes

mp

103-107 °C (lit.)

储存温度

2-8°C

SMILES string

CC(C)(C)S(N)=O

InChI

1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1

InChI key

CESUXLKAADQNTB-SSDOTTSWSA-N

一般描述

(R)-(+)-2-甲基-2-丙烷亚磺酰胺是一种手性助剂，用于醛的缩合。

应用

Ellman 亚磺酰胺类

( R )-(+)-2-甲基-2-丙亚磺酰胺可用于通过铜介导与环己烷甲醛缩合制备 N -（1-环己基亚甲基）-2-甲基丙-2-亚磺酰胺。也可用于制备 (20E)-N-[t-丁基-(R)-亚磺酰基]-3β-（ t -丁基二甲基硅氧烷）-孕甾-5-烯-20-亚胺，开发雄激素受体拮抗剂的中间体。

可通过与醛酮缩合易转化为 P,N -亚磺酰亚胺配体，后者可进行铱催化的烯烃不对称氢化反应。

手性氮杂环丁烷合成中 ß-氯亚磺酰胺的制备。也用于制备有机催化剂，用于亚胺的对映选择性还原。

用于合成手性胺的有用试剂。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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示例

T1503

货号

25G

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705578-5MG-PW

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Use of alpha-chlorinated N-(tert-butanesulfinyl)imines in the synthesis of chiral aziridines.

Bram Denolf et al.

Organic letters, 8(14), 3129-3132 (2006-06-30)

[reaction: see text] Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with

A stereoselective synthesis of (S)-2-(((3-fluoro-4-methylphenoxy) carbonyl)(1-(4-((5-methyl-2-phenyloxazol-4-yl) methoxy) phenyl) ethyl) amino) acetic acid, a highly potent PPAR alpha gamma dual agonist

Xinhua Q et al.

Tetrahedron, 71, 9408-9414 (2015)

20-Aminosteroids as a novel class of selective and complete androgen receptor antagonists and inhibitors of prostate cancer cell growth.

Fousteris MA, et al.

Bioorganic & Medicinal Chemistry, 18(19), 6960-6969 (2010)

Highly stereoselective addition of organometallic reagents to N-tert-butanesulfinyl imines derived from 3- and 4-substituted cyclohexanones.

Jeffrey P McMahon et al.

Organic letters, 6(10), 1645-1647 (2004-05-07)

Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group

Asymmetric synthesis of a, a-difluoro-?-amino acid derivatives from enantiomerically pure N-tert-butylsulfinimines.

Staas, DD, et al.

The Journal of Organic Chemistry, 67(23), 8276-8279 (2002)

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Ellman's Sulfinamides

Ellman's sulfinamide is available in both enantiomeric and racemic forms for your research. This versatile and useful auxiliary has found extensive use both in academics and industry.

相关内容

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

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