127184-04-7

Basic information

• Product Name: (3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide
• Synonyms: (1S)-(-)-(7,7-Dichloro-10-caMphorsulfonyl)iMine;(3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide
• CAS NO: 127184-04-7
• Molecular Formula: C10H13Cl2NO2S
• Molecular Weight: 282.18672
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 127184-04-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: (3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide(127184-04-7)
• EPA Substance Registry System: (3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide(127184-04-7)

Safety Data

• Hazardous Substances Data: 127184-04-7(Hazardous Substances Data)

Usage

Description

(3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide is a pale yellow solid with unique chemical properties. It is a complex organic compound characterized by its specific stereochemistry and functional groups, making it a valuable synthetic intermediate in chemical synthesis.

Uses

Used in Pharmaceutical Industry:
(3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and properties allow it to be a key component in the synthesis of various drugs, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, (3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide serves as a versatile building block for the creation of a wide range of organic compounds. Its reactivity and structural features make it suitable for various synthetic routes, enabling the production of diverse chemical entities with potential applications in various industries.
Used in Research and Development:
(3aS,6S)-7,7-Dichloro-4,5,6,7-tetrahydro-8,8-diMethyl-3H-3a,6-Methano-2,1-benzisothiazole 2,2-Dioxide is also utilized in research and development settings. Its unique properties and reactivity make it an interesting subject for scientific studies, potentially leading to new discoveries and innovations in the field of chemistry and related disciplines.

Upstream product

• 60886-80-8 (1S)-(-)-camphorsulfonylimine 

Downstream Products

• 127184-05-8 (+)-((8,8-Dichlorocamphoryl)sulfonyl)oxaziridine 

Relevant articles and documents

Asymmetric Fluorination of Enolates with Nonracemic N-Fluoro-2,10-Camphorsultams

The asymmetric "electrophilic" fluorination of tertiary enolates by nonracemic N-fluoro-2,10-camphorsultams 3 affords quaternary α-fluoro carbonyl compounds in modest yield and ee. The highest asymmetric induction was observed for the fluorination of the sodium enolate of 2-methyl-1-tetralone (8a) by (-)-N-fluoro-2,10-(3,3-dichlorocamphorsultam) (3b) to give (S)-(+)-2-fluoro-2-methyl-1-tetralone (9a) in 70percent ee. The absolute configuration was established by X-ray crystallography of the corresponding diastereomeric β-hydroxy sulfoximine prepared from (±)-9a and the Johnson reagent. The asymmetric induction exhibited by 3 is opposite to that of the closely related enolate hydroxylation reagents nonracemic (camphorylsulfonyl)oxaziridines 4. The N-fluoro sultams 3 were prepared by fluorination (10percent F2/N2) of the corresponding sultams 5.

(+)-(2R,8aR)-[(8,8-Dimethoxycamphoryl)sulfonyl]oxaziridine and (+)- (2R,8aR)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine: [[4H-4a,7-Methanooxazirino[3,2-i][2,1]benzisothiazole, tetrahydro-8,8-dimethoxy-9,9-dimethyl-, 3,3-dioxide], [2R-(2α,4aα,7α,8aR)]- and [4H-4a,7-Methanooxazirino[3,2-i][2,1]benzisothiazole, 8,8-dichlorotetrahydro-9,9-dimethyl-, 3,3-dioxide, [2R- (2α,4aα,7α,8aR)]]

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A convenient, improved synthesis of (camphoryl)sulfonyl oxaziridines

A convenient, efficient procedure for the large scale synthesis of chiral oxidizing reagents (+), and (-)-((8,8-dichlorocamphory)sulfonyl)oxaziridine, 5, as well as of 8,8 unsubstituted (+), and (-) (camphoryl)sulfonyl oxaziridine, 4, from (+), or (-) (camphoryl)imine, 2, in step yields of 83% to 95%, is reported.