(2S,3R)-2-methyl-3-phenylaziridine

Base Information

• Chemical Name: (2S,3R)-2-methyl-3-phenylaziridine
• CAS No.: 61091-41-6
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.193
• UNII: 5JWH8ZR638
• Nikkaji Number: J893.216F
• Mol file: 61091-41-6.mol

Synonyms:(2S,3R)-2-methyl-3-phenylaziridine;61091-41-6;5JWH8ZR638;SCHEMBL18978386;Aziridine, 2-methyl-3-phenyl-, (2S,3R)-;AZIRIDINE, 2-METHYL-3-PHENYL-, (2S-CIS)-;(-)-(2S,3R)-CIS-2-METHYL-3-PHENYLAZIRIDINE

Chemical Property of (2S,3R)-2-methyl-3-phenylaziridine

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(N1)C2=CC=CC=C2
• Isomeric SMILES: C[C@H]1[C@H](N1)C2=CC=CC=C2

Technology Process of (2S,3R)-2-methyl-3-phenylaziridine

There total 7 articles about (2S,3R)-2-methyl-3-phenylaziridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

2-methyl-3-phenyl-1-{[2-(trimethylsilyl)ethane]sulfonyl}aziridine (1384685-19-1) → (-)-(2S,3R)-cis-2-methyl-3-phenylaziridine (1485-13-8,7763-71-5,13148-30-6,13452-28-3,20993-60-6,61091-40-5,61091-41-6)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/c2cc32997b

Reference yield: 57.0%

(1S,2S)-(+)-1-chloro-1-phenyl-2-propylamine hydrochloride → (-)-(2S,3R)-cis-2-methyl-3-phenylaziridine (1485-13-8,7763-71-5,13148-30-6,13452-28-3,20993-60-6,61091-40-5,61091-41-6)

Guidance literature:

With sodium hydroxide; at 80 ℃;

DOI:10.1016/S0022-328X(00)00520-9

Reference yield: 50.0%

(1R,2R)-(-)-1-chloro-1-phenyl-2-propylamine hydrochloride → (-)-(2S,3R)-cis-2-methyl-3-phenylaziridine (1485-13-8,7763-71-5,13148-30-6,13452-28-3,20993-60-6,61091-40-5,61091-41-6)

Guidance literature:

With sodium hydroxide; at 80 ℃; for 2h;

DOI:10.1021/ol050094n

upstream raw materials:

(1S,2R)-(+)-norphedrine

(1R,2S)-(-)-norephedrine hydrochloride

2-methyl-3-phenyl-1-{[2-(trimethylsilyl)ethane]sulfonyl}aziridine

cis-1-phenyl-1-propylene

Downstream raw materials:

(4S,5S)-trans-4-methyl-5-phenyl-thiazolidinethione

[5-tert-butoxycarbonylamino-5-(1-methyl-2-phenylethylcarbamoyl)pentyl]carbamic acid tert-butyl ester

(+)-(1S,2S)-(2-benzylamino-1-phenylpropyl)diphenylphosphane

Refernces

• 1、 Kim, Chungsik,Uchida, Tatsuya,Katsuki, Tsutomu. "Asymmetric olefin aziridination using a newly designed Ru(CO)(salen) complex as the catalyst". supporting information; experimental part. p. 7188 - 7190. Retrieved 2012/07/31.
• 2、 Dalili, Shadi,Yudin, Andrei K.. "Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines". . p. 1161 - 1164. Retrieved 2007/10/03.