(3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester

Base Information

• Chemical Name: (3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester
• CAS No.: 220586-54-9
• Molecular Formula: C12H18NO3P
• Molecular Weight: 255.254
• DSSTox Substance ID: DTXSID50449763
• Nikkaji Number: J1.031.588C
• Wikidata: Q82269278
• Mol file: 220586-54-9.mol

Synonyms:CTK0I8866;DTXSID50449763;220586-54-9;(3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester

Chemical Property of (3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 255.10243043
• Heavy Atom Count: 17
• Complexity: 282

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1C(N1)C2=CC=CC=C2)OCC
• Isomeric SMILES: CCOP(=O)([C@H]1[C@H](N1)C2=CC=CC=C2)OCC

Technology Process of (3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester

There total 11 articles about (3beta-Phenylaziridine-2beta-yl)phosphonic acid diethyl ester 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: 91.0%

diethyl(-)-S-(3-phenyl-2-H-azirin-2-yl) phosphonate (220586-49-2) → diethyl(-)-(2S,3R)-(3-phenyl-2-H-aziridin-2-yl) phosphonate (220586-54-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃;

DOI:10.1016/S0957-4166(03)00089-2

Reference yield: 84.0%

diethyl (Ss,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate (220586-52-7) → diethyl(-)-(2S,3R)-(3-phenyl-2-H-aziridin-2-yl) phosphonate (220586-54-9)

Guidance literature:

With trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(98)02331-4

Reference yield: 77.0%

diethyl (SS,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate (607729-55-5) → diethyl(-)-(2S,3R)-(3-phenyl-2-H-aziridin-2-yl) phosphonate (220586-54-9)

Guidance literature:

With methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;

DOI:10.1021/jo030142m

upstream raw materials:

diethyl (S_s,2S,3R)-(-)-N-(p-toluenesulfinyl)-3-phenylaziridine-2-phosphonate

diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate

diethyl(-)-S-(3-phenyl-2-H-azirin-2-yl) phosphonate

diethyl iodomethanephosphonate

Downstream raw materials:

(S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester

diethyl(-)-S-(3-phenyl-2-H-azirin-2-yl) phosphonate

diethyl(-)-(2S,3R)-[3-phenyl-1-p-toluenesulfonyl-aziridin-2-yl] phosphonate

diethyl(+)-(3S)-[2-phenyl-1-(p-toluenesulfonylamino)ethyl] phosphonate