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文件

497401

Sigma-Aldrich

( R )-(+)-2-甲基-2-丙亚磺酰胺

98%

同義詞:

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

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About This Item

線性公式:
(CH3)3CS(O)NH2
CAS號碼:
196929-78-9
分子量：:
121.20
MDL號碼:
MFCD05861479
分類程式碼代碼:
12352111
PubChem物質ID:
24873117
NACRES:
NA.22

化驗

98%

光學活性

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

mp

103-107 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

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

InChI

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

InChI 密鑰

CESUXLKAADQNTB-SSDOTTSWSA-N

相關類別

一般說明

(R)-(+)-2-甲基-2-丙烷亚磺酰胺是一种手性助剂，用于醛的缩合。

應用

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。

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)

分析證明 (COA)

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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
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)
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)
Dong Pei et al.
Organic letters, 8(25), 5913-5915 (2006-12-01)
Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broad range of N-aryl
Journal of the American Chemical Society, 119, 9913-9914 (1997)
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文章

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.

Ellman's Sulfinamides

Ellman 的亞磺酰胺有對映體和外消旋體兩種形式，可供您進行研究。這種多用途的有用輔助劑在學術界和工業界都有廣泛的應用。

相關內容

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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