Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)-

Base Information

• Chemical Name: Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)-
• CAS No.: 13148-28-2
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• DSSTox Substance ID: DTXSID10443929
• Nikkaji Number: J411.022F
• Mol file: 13148-28-2.mol

Synonyms:Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)-;13148-28-2;DTXSID10443929;(2S)-1,2beta-Dimethyl-3alpha-phenylaziridine

Chemical Property of Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.104799419
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(N1C)C2=CC=CC=C2
• Isomeric SMILES: C[C@H]1[C@@H](N1C)C2=CC=CC=C2

Technology Process of Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)-

There total 18 articles about Aziridine, 1,2-dimethyl-3-phenyl-, (2S,3S)- 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: 89.0%

ephedrine (299-42-3,7009-81-6,90-83-5,6912-63-6) → (+)-(2S,3S)-trans-1,2-dimethyl-3-phenylaziridine (13148-28-2)

Guidance literature:

With diethyl azodicarbodiimide; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 10h;

DOI:10.1021/jo016058t

Reference yield: 84.0%

(-)-erythro-Ephedrine (90-81-3,90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,7009-81-6,90-83-5,6912-63-6) → (+)-(2S,3S)-trans-1,2-dimethyl-3-phenylaziridine (13148-28-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; for 2h; Ambient temperature;

DOI:10.1055/s-1984-31041

Reference yield: 32.0%

1-propenylbenzene (873-66-5) + tert-butyl (((chloromethyl)sulfonyl)oxy)(methyl)carbamate → trans-(2S,3S)-N-methyl-2-methyl-3-phenylaziridine (936-42-5,936-43-6,2242-90-2,13148-28-2,60761-45-7,68277-68-9,124919-00-2)

Guidance literature:

With trifluoroacetic acid; In 2,2,2-trifluoroethanol; at 20 ℃; for 48h; diastereospecific reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.8b10485

upstream raw materials:

ephedrine

sodium ethanolate

(-)-erythro-Ephedrine

((1S,2R)-2-Bromo-1-methyl-2-phenyl-ethyl)-methyl-amine; hydrochloride

Downstream raw materials:

(4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione

(αR,βS)-α,N-dimethyl-β-(phenylthio)benzeneethanamine

(2S,5R)-3-(N-methyl)-4-methyl-5-phenyl-2,2-dimethyl-1,3-thiazolane

(1R,2S)-1-phenyl-2-(N-methyl-N-acetamido)propanethiol

Refernces

• 1、 De Ceglie, Maria Carolina,Musio, Biagia,Affortunato, Francesco,Moliterni, Anna,Altomare, Angela,Florio, Saverio,Luisi, Renzo. "Solvent- and temperature-dependent functionalisation of enantioenriched aziridines". scheme or table. p. 286 - 296. Retrieved 2011/02/27.
• 2、 Hsu,Fang. "Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan". . p. 8573 - 8584. Retrieved 2007/10/03.