(3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide

Base Information

• Chemical Name: (3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide
• CAS No.: 204990-17-0
• Molecular Formula: C₁₆H₂₆N₃OP
• Molecular Weight: 307.376
• DSSTox Substance ID: DTXSID50443862
• Nikkaji Number: J1.183.605D
• Wikidata: Q82261836
• Mol file: 204990-17-0.mol

Synonyms:(3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide;204990-17-0;DTXSID50443862;AKOS025294860;J-013361;(3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide, >=98.0% (HPLC);(3Ar,7ar)-1,3-dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide

Chemical Property of (3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide

Chemical Property:

• Melting Point: 135-140 °C
• PSA: 45.39000
• LogP: 3.90040
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 307.18134946
• Heavy Atom Count: 21
• Complexity: 388

Purity/Quality:

97% ^*data from raw suppliers

(3A,7AR)-1,3-DIMETHYL-N-[(1S)-1-PHENYLETHYL]OCTAHYDRO-1H-1,3,2-BENZODIAZAPHOSPHOL-2-AMINE 2-OXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NP2(=O)N(C3CCCCC3N2C)C
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)NP2(=O)N([C@@H]3CCCC[C@H]3N2C)C

Technology Process of (3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide

There total 4 articles about (3a,7aR)-1,3-Dimethyl-N-[(1S)-1-phenylethyl]octahydro-1H-1,3,2-benzodiazaphosphol-2-amine 2-oxide 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: 44.0%

(R)-1-phenyl-ethyl-amine (3886-69-9) + (3aR,7aR)-2-chloro-1,3-dimethyloctahydro-1H-1,3,2-benzodiazaphosphole 2-oxide (137943-77-2) → ((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-((R)-1-phenyl-ethyl)-amine (204990-17-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) 0 deg C, 20 min; r.t., 10 min, 2.) r.t., 12 h;

DOI:10.1039/a709174e

Reference yield: 36.0%

(S)-1-phenyl-ethylamine (2627-86-3) + (3aR,7aR)-2-chloro-1,3-dimethyloctahydro-1H-1,3,2-benzodiazaphosphole 2-oxide (137943-77-2) → ((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-((S)-1-phenyl-ethyl)-amine (204990-17-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) 0 deg C, 20 min; r.t., 10 min, 2.) r.t., 12 h;

DOI:10.1039/a709174e

Reference yield:

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5) → ((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-((R)-1-phenyl-ethyl)-amine (204990-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NEt₃, POCl₃ / CH₂Cl₂ / 12 h / Ambient temperature

2: 44 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min; r.t., 10 min, 2.) r.t., 12 h

With n-butyllithium; triethylamine; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/a709174e

upstream raw materials:

(R)-1-phenyl-ethyl-amine

(3aR,7aR)-2-chloro-1,3-dimethyloctahydro-1H-1,3,2-benzodiazaphosphole 2-oxide

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

(S)-1-phenyl-ethylamine