(1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene

Base Information

• Chemical Name: (1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene
• CAS No.: 57466-29-2
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.181

Synonyms:

Chemical Property of (1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene

Chemical Property:

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Technology Process of (1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene

There total 14 articles about (1S)-(-)-cis-1-acetoxy-4-hydroxy-2-cyclohexene 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: 74.0%

cis-4-(tert-butyldimethylsilyloxy)cyclohex-2-enyl acetate → cis-2-cyclohexene-1,4-diol monoacetate (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1039/b916506a

Reference yield: 70.0%

copper diacetate (142-71-2) + 3,4-epoxycyclohexene (6705-51-7) → cis-2-cyclohexene-1,4-diol monoacetate (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3)

Guidance literature:

In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/S0040-4039(00)81431-8

Reference yield: 61.0%

trans-4-acetoxy-1-trifluoroacetoxy-cyclohex-2-ene (91923-19-2) → Acetic acid (1S,4S)-4-hydroxy-cyclohex-2-enyl ester (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3) + cis-2-cyclohexene-1,4-diol monoacetate (57466-29-2,86210-23-3,86210-32-4,132617-05-1,132617-15-3,136779-08-3)

Guidance literature:

With water; In methanol; for 19h; Yields of byproduct given. Title compound not separated from byproducts; silica;

DOI:10.1016/S0040-4039(01)81271-5

upstream raw materials:

rac-3-acetoxycyclohexene

3,4-epoxycyclohexene

acetyl chloride

trans-4-acetoxy-1-trifluoroacetoxy-cyclohex-2-ene

Downstream raw materials:

4-(acetoxy)cyclohex-2-enone

cyclohexenone

trans-4-chloro-2-cyclohexen-1-yl acetate

(1S,4S)-4-Butyl-cyclohex-2-enol

Refernces

Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate

10.1021/ol060692h

The research focuses on developing a method to synthesize cannabidiol (CBD) and its analogues. The study highlights the potential of CBD as a nonpsychotropic drug due to its lack of binding to receptors responsible for psychoactivity, unlike ?9-tetrahydrocannabinol (?9-THC). The key reaction involves nickel-catalyzed allylation of 2-cyclohexene-1,4-diol monoacetate using a new reagent system, (alkenyl)ZnCl/TMEDA, achieving 94% regioselectivity and good yield. This method allows for the synthesis of CBD and its analogues, including those with longer alkenyl side chains. The research also explores the synthesis of metabolites like 7-hydroxy-CBD and demonstrates the transformation of synthesized compounds into CBD and ?9-THC. Chemicals such as lithium isopropenyl borate, alkenyl Grignard reagents, and various metal catalysts (e.g., NiCl2(tpp)2) play crucial roles in achieving the desired products with high regioselectivity and yield.

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