5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]-

Base Information

• Chemical Name: 5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]-
• CAS No.: 122331-40-2
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• DSSTox Substance ID: DTXSID201167516
• Nikkaji Number: J439.752E
• Mol file: 122331-40-2.mol

Synonyms:DTXSID201167516;122331-40-2;5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]-

Chemical Property of 5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]-

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 221

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1CC(=NO1)C2=CC=CC=C2)O
• Isomeric SMILES: C[C@H]([C@@H]1CC(=NO1)C2=CC=CC=C2)O

Technology Process of 5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]-

There total 4 articles about 5-Isoxazolemethanol, 4,5-dihydro-alpha-methyl-3-phenyl-, [S-(R*,S*)]- 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: 46.0%

(S)-(4,5-dihydro-3-phenyl-5-isoxazolyl)ethanone (122331-42-4) → (αS)-threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol (121523-84-0) + (1R)-1-<(5S)-4,5-dihydro-3-phenyl-5-isoxazolyl>ethanol (122331-40-2)

Guidance literature:

With potassium borohydride; potassium bromide; In water; at 0 ℃; for 0.25h; Yield given;

Reference yield:

5-acetyl-4,5-dihydro-3-phenylisoxazole (54606-00-7) → (1R)-1-<(5S)-4,5-dihydro-3-phenyl-5-isoxazolyl>ethanol (122331-40-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / propan-2-ol; H₂O / 9 h / 30 °C / dry yeast, 2-propanol/water(4:1)

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -60 deg C to RT

3: 46 percent / 3 M KBr, KBH₄ / H₂O / 0.25 h / 0 °C

With potassium borohydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; potassium bromide; In water; isopropyl alcohol;

Reference yield:

(αS)-threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol (121523-84-0) → (1R)-1-<(5S)-4,5-dihydro-3-phenyl-5-isoxazolyl>ethanol (122331-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -60 deg C to RT

2: 46 percent / 3 M KBr, KBH₄ / H₂O / 0.25 h / 0 °C

With potassium borohydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; potassium bromide; In water;

upstream raw materials:

(S)-(4,5-dihydro-3-phenyl-5-isoxazolyl)ethanone

5-acetyl-4,5-dihydro-3-phenylisoxazole

(αS)-threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol

Downstream raw materials:

(S)-(4,5-dihydro-3-phenyl-5-isoxazolyl)ethanone