127392-81-8

Basic information

• Product Name: 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one
• Synonyms: 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one
• CAS NO: 127392-81-8
• Molecular Weight: 347.478
• Mol File: 127392-81-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one(127392-81-8)
• EPA Substance Registry System: 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one(127392-81-8)

Safety Data

• Hazardous Substances Data: 127392-81-8(Hazardous Substances Data)

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 94594-90-8 (2R)-bornane-10,2-sultam 

Downstream Products

• 127392-94-3 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-3-phenyl-propan-1-one 
• 787635-22-7 1,1-dimethylethyl (3S)-4-[(3aS,6R,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoate 
• 129568-84-9 (2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam 
• 35016-65-0 (2R)-(N-hydroxy)phenylalanine 
• 673-06-3 D-(R)-phenylalanine 
• 787635-24-9 (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 145375-43-5 mitiglinide 
• 787635-23-8 (3S)-4-[(3aS,6R,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoic acid 
• 337518-87-3 (S)-4-(tert-butoxy)-4-oxo-2-(1-phenylmethyl)butanoic acid 
• 3972-36-9 (2S)-benzylsuccinic acid 
• 129505-09-5 (2R,2'R)-N-<2'-(hydroxyamino)-3'-phenylpropanoyl>bornane-10,2-sultam 

Relevant articles and documents

A practical and efficient preparation of (S)-2-benzylsuccinic acid: A key acid synthon of KAD-1229

This report describes a practical and an efficient synthesis of (S)-2-benzyl-succinic acid, which was employed as a key intermediate for hypoglycemic KAD-1229 by means of asymmetric alkylation of N-acylsultam. The condensation of D-(-)-camphorsultam with 3-phenylpropionyl chloride gave N-acylsultam 1. N-acylsultam 1 reacted with 1.1 equimolar amount of sodium amide base to form chiral enolate, followed by alkylation with tert-butyl bromoacetate to afford 2. Cleavage of ester and saponification with H 2O2-LiOH provided the desired compound 5 with excellent yield and high optical purity.

Electrophilic trifluoromethylthiolation of carbonyl compounds

A general method for the α-trifluoromethylthiolation of carbonyl compounds, without prefunctionalization, has been developed. Aldehydes, ketones, esters, amides, keto-esters, alkaloids, and steroids have been trifluoromethylthiolated with good yields. This work, proposing a new reagent for electrophilic trifluoromethylthiolation, provides a route towards the original synthesis of various trifluoromethylthiolated molecules for further applications.

Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-Chloro-1-nitrosocyclohexane as a Practical +> Equivalent

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq.HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5.These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (S,S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.