(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide

Base Information

• Chemical Name: (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide
• CAS No.: 1331747-24-0
• Molecular Formula: C₁₆H₂₀F₃NO₃
• Molecular Weight: 331.335
• Mol file: 1331747-24-0.mol

Synonyms:(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide

Chemical Property of (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide

There total 1 articles about (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide 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:

homoalylic alcohol (627-27-0) + N-(4-methoxyphenyl)-N-(1,1,1-trifluoropent-4-en-2-yl)acetamide (1190108-24-7) → hex-3-ene-1,6-diol (67077-43-4) + (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide (1331747-24-0) + (E)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide (1262405-40-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dichloro-1,4-benzoquinone; In dichloromethane; for 108h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1039/c0ob00308e

Reference yield: 54.0%

(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide (1331747-24-0) + p-methoxybenzyl chloride (824-94-2) → (Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-(4-methoxybenzyloxy)hept-4-en-2-yl)acetamide (1262405-46-8)

Guidance literature:

(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 0 ℃; Inert atmosphere;

p-methoxybenzyl chloride; In dimethyl sulfoxide; mineral oil; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c0ob00308e

Reference yield:

(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-hydroxyhept-4-en-2-yl)acetamide (1331747-24-0) + p-methoxybenzyl chloride (824-94-2) → (1R*,3R*,5R*,6R*)-6-(2-(4-methoxybenzyloxy)ethyl)-2-(4-methoxyphenyl)-1-methyl-3-(trifluoromethyl)-2-azabicyclo[3.1.0]hexane + (1R*,3S*,5R*,6R*)-6-(2-(4-methoxybenzyloxy)ethyl)-2-(4-methoxyphenyl)-1-methyl-3-(trifluoromethyl)-2-azabicyclo[3.1.0]hexane

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0 °C / Inert atmosphere

1.2: 24 h / 0 - 20 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; cyclopentylmagnesium chloride / diethyl ether / 0.5 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium hydride; cyclopentylmagnesium chloride; In diethyl ether; dimethyl sulfoxide; mineral oil; 2.1: Intramolecular Kulinkovich-de Meijere reaction;

DOI:10.1039/c0ob00308e

upstream raw materials:

homoalylic alcohol

N-(4-methoxyphenyl)-N-(1,1,1-trifluoropent-4-en-2-yl)acetamide

Downstream raw materials:

(Z)-N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-7-(4-methoxybenzyloxy)hept-4-en-2-yl)acetamide