(Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Base Information

• Chemical Name: (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone
• CAS No.: 160618-28-0
• Molecular Formula: C₁₉H₂₂Br₂O₄
• Molecular Weight: 474.189
• Mol file: 160618-28-0.mol

Synonyms:(Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Chemical Property of (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone

There total 5 articles about (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone 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: 68.0%

<1'R-(1'α,2'α,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one (128260-47-9) → (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone (160618-28-0)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 2h;

DOI:10.1021/jo00101a031

Reference yield: 61.0%

<1'R-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one (160707-50-6) → (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone (160618-28-0)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; at 0 ℃; for 0.5h;

DOI:10.1021/jo00101a031

Reference yield:

(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-4,6-dimethoxy-2-(methanesulfonyloxy)phenyl)ethanone (160618-31-5) → (Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone (160618-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Na₂CO₃ / aq. ethanol / 0.33 h / 70 °C

2: Na₂CO₃ / ethanol / other catalysts

3: 61 percent / n-BuLi / diethyl ether; hexane / 0.5 h / 0 °C

With n-butyllithium; sodium carbonate; sodium carbonate; In diethyl ether; ethanol; hexane;

DOI:10.1021/jo00101a031

upstream raw materials:

<1'R-(1'α,2'β,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

<1'R-(1'α,2'α,5'α)>-6,8-dibromo-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-4,6-dimethoxy-2-(methanesulfonyloxy)phenyl)ethanone

(E)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone