(2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol

Base Information

• Chemical Name: (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol
• CAS No.: 436806-96-1
• Molecular Formula: C₂₂H₂₁NO₃
• Molecular Weight: 347.414
• Mol file: 436806-96-1.mol

Synonyms:(2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol

Chemical Property of (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol

There total 1 articles about (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol 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: 86.0%

2-allyloxy-1-naphthaldehyde (19530-43-9) + (R)-α-(hydroxymethyl)benzylhydroxylamine (321174-47-4) → (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol (436806-96-1)

Guidance literature:

With magnesium sulfate; acetic acid; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo011015y

Reference yield: 89.0%

(2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol (436806-96-1) → (2R)-2-((3aR,11cS)-3a,11c-dihydro-3H-benzo[5,6]chromeno[4,3-c]isoxazol-1(4H)-yl)-2-phenylethanol + (2R)-2-((3aS,11cR)-3a,11c-dihydro-3H-benzo[5,6]chromeno[4,3-c]isoxazol-1(4H)-yl)-2-phenylethanol (436807-00-0)

Guidance literature:

With zinc trifluoromethanesulfonate; triethylamine; In dichloromethane; at 40 ℃; for 68h;

DOI:10.1021/jo011015y

Reference yield:

(2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol (436806-96-1) → N-[(1R,2R)-2-(hydroxymethyl)-2,3-dihydro-1H-benzo[f]chromen-1-yl]-N-methyl-N'-[3-(trifluoromethyl)phenyl]thiourea (321574-22-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 68 h / 40 °C

2.1: methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 3 h / 20 °C

2.2: KH / 2-methyl-propan-2-ol / 18 h / 40 °C

2.3: 85 percent / aq. HCl / tetrahydrofuran / 6 h

3.1: 92 percent / Zn; aq. AcOH / tetrahydrofuran / 55 °C

4.1: Et₃N / tetrahydrofuran / 2 h / 20 °C

4.2: 88 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

5.1: 95 percent / tetrahydrofuran / 15 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; acetic acid; methanesulfonyl chloride; triethylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo011015y

upstream raw materials:

2-allyloxy-1-naphthaldehyde

(R)-α-(hydroxymethyl)benzylhydroxylamine

Downstream raw materials:

(2R)-2-((3aS,11cR)-3a,11c-dihydro-3H-benzo[5,6]chromeno[4,3-c]isoxazol-1(4H)-yl)-2-phenylethanol

(3aS,11cR)-1,3a,4,11c-tetrahydro-3H-benzo[5,6]chromeno[4,3-c]isoxazole

N-[(1R,2R)-2-(hydroxymethyl)-2,3-dihydro-1H-benzo[f]chromen-1-yl]-N-methyl-N'-[3-(trifluoromethyl)phenyl]thiourea