Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)-

Base Information

• Chemical Name: Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)-
• CAS No.: 200411-28-5
• Molecular Formula: C18H22NOP
• Molecular Weight: 299.353
• DSSTox Substance ID: DTXSID40449378
• Nikkaji Number: J920.263C
• Mol file: 200411-28-5.mol

Synonyms:200411-28-5;(R)-(2-Butylaziridin-1-yl)diphenylphosphine oxide;Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)-;DTXSID40449378;(2R)-1-(Diphenylphosphinyl)-2-butylaziridine

Chemical Property of Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)-

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 299.143901323
• Heavy Atom Count: 21
• Complexity: 349

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1CN1P(=O)(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: CCCC[C@@H]1CN1P(=O)(C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)-

There total 5 articles about Aziridine, 2-butyl-1-(diphenylphosphinyl)-, (2R)- 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: 62.0%

n-propylmagnesium bromide (927-77-5) + (2R)-N,O-bis(diphenylphosphinyl)-2-(hydroxymethyl)aziridine (582314-57-6) → (2R)-(+)-N-(diphenylphosphinyl)-2-butylaziridine (200411-28-5)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/S0040-4020(03)00551-9

Reference yield:

(2S)-1-azido-(+)-3-O-(diphenylphosphoryl)propane-2,3-diol (582314-55-4) → (2R)-(+)-N-(diphenylphosphinyl)-2-butylaziridine (200411-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Ph₃P / acetonitrile / 2 h / Heating

1.2: 29 percent / triethylamine / CH₂Cl₂ / 20 °C

2.1: 62 percent / CuBr*SMe₂ / tetrahydrofuran / 0.5 h / Heating

With copper(I) bromide dimethylsulfide complex; triphenylphosphine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4020(03)00551-9

Reference yield:

(2R)-(+)-(O-diphenylphosphoryl)-2-(hydroxymethyl)oxirane (582314-54-3) → (2R)-(+)-N-(diphenylphosphinyl)-2-butylaziridine (200411-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / NaN₃; NH₄Cl / methanol / 3 h / Heating

2.1: Ph₃P / acetonitrile / 2 h / Heating

2.2: 29 percent / triethylamine / CH₂Cl₂ / 20 °C

3.1: 62 percent / CuBr*SMe₂ / tetrahydrofuran / 0.5 h / Heating

With sodium azide; copper(I) bromide dimethylsulfide complex; ammonium chloride; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/S0040-4020(03)00551-9

upstream raw materials:

(2R)-2-amino-2-butyl-1-ethanol

Diphenylphosphinic chloride

n-propylmagnesium bromide

(2R)-N,O-bis(diphenylphosphinyl)-2-(hydroxymethyl)aziridine

Downstream raw materials:

(1R,3R,5S,8aS)-1-Benzenesulfonyl-3-butyl-5-methyl-octahydro-indolizine

Acetic acid (R)-2-benzenesulfonyl-4-benzoylamino-1-pent-4-enyl-octyl ester

5-((2S,3R,5R)-3-Benzenesulfonyl-1-benzyl-5-butyl-pyrrolidin-2-yl)-pentan-2-one

((2S,3R,5R)-3-Benzenesulfonyl-5-butyl-2-pent-4-enyl-pyrrolidin-1-yl)-phenyl-methanone