(1β,3α,5β)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid

Base Information

• Chemical Name: (1β,3α,5β)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid
• CAS No.: 21932-98-9
• Molecular Formula: C10H14O2
• Molecular Weight: 166.21700
• Mol file: 21932-98-9.mol

Synonyms:bicyclo<3.3.1>non-6-ene-3-carboxylic acid;endo-bicyclo[3.3.1]non-6-ene-3-carboxylic acid;endo-bicyclo<3.3.1>non-6-en-3-carboxylic acid;endo-Bicyclo<3.3.1>non-6-ene-3-carboxylic acid;(1S,3S,5R)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid;endo-Bicyclo<3.3.1>non-2-en-7-carbonsaeure;bicyclo<3.3.1>non-6-ene-endo-3-carboxylic acid;

Chemical Property of (1β,3α,5β)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid

Chemical Property:

• Boiling Point: 296.6±29.0 °C(Predicted)
• PKA: 4.70±0.20(Predicted)
• PSA: 37.30000
• Density: 1.136±0.06 g/cm3(Predicted)
• LogP: 2.06340

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1β,3α,5β)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid

There total 5 articles about (1β,3α,5β)-Bicyclo[3.3.1]non-6-ene-3-carboxylic acid 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: 80.0%

2-Adamantanone (700-58-3) → endo-Bicyclo<3.3.1>non-6-ene-3-carboxylic acid (21932-98-9)

Guidance literature:

With sodium azide; methanesulfonic acid;

DOI:10.1021/jo00169a066

Reference yield:

exo-7-hydroxybicyclo[3.3.1]nonane-3-carboxylic acid → (+)-endo-bicyclo<3.3.1>non-6-ene-3R-carboxylic acid (21932-98-9,26768-58-1,56820-19-0,64889-20-9,64937-51-5,72028-71-8,103364-84-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 2h; Reflux;

Reference yield:

1-adamantanol (700-57-2) → endo-Bicyclo<3.3.1>non-6-ene-3-carboxylic acid (21932-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hypochlorite; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 0.33 h / 0 °C / Inert atmosphere

2.1: sodium azide; methanesulfonic acid / 2 h / 35 °C / Inert atmosphere

2.2: 35 °C / Inert atmosphere

With sodium hypochlorite; sodium azide; methanesulfonic acid; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water;

DOI:10.1055/s-0030-1260257

upstream raw materials:

2-Adamantanone

1-adamantanol

Downstream raw materials:

(+)-(1S,5R)-endo-(3(R)-bicyclo<3.3.1>non-6-enyl) methyl ketone

4^e-chloroadamantan-2-one

4^a-chloroadamantan-2-one

4-Hydroxyadamantan-2-on

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