Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-
• CAS No.: 464-78-8
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Mol file: 464-78-8.mol

Synonyms:Ketopinic acid;7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid;Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-;(1S)-(+)-Ketopinic acid;(S)-(+)-Ketopinic acid;(S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid;2-Oxo-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid;2-Oxobornane-10-oic acid;

Chemical Property of Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-

Chemical Property:

• Melting Point: 233-234 °C
• Boiling Point: 313.3 °C at 760 mmHg
• PKA: 3.67±0.40(Predicted)
• Flash Point: 157.5 °C
• PSA: 54.37000
• Density: 1.238 g/cm³
• LogP: 1.46640
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ketopinicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic Acid is a useful reactant for the preparation of alkenyl nitrile electrophiles for the possible use of covalent protein labeling.

Technology Process of Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-

There total 44 articles about Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo- 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: 95.0%

(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester (125637-45-8) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

Alkaline hydrolysis;

DOI:10.1007/s11178-005-0022-4

Reference yield: 90.0%

(1S)-10-camphorsulfonic acid (3144-16-9,61380-66-3) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

(1S)-10-camphorsulfonic acid; With thionyl chloride; for 1.5h; Reflux;

With potassium permanganate; potassium carbonate; In water monomer; acetonitrile; at 70 - 80 ℃; for 48h;

With anhydrous potassium sulfite; sulfuric acid;

DOI:10.1016/j.bmcl.2021.128465

Reference yield: 87.0%

Camphorsulfonyl chloride (21286-54-4) → (1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2)

Guidance literature:

With potassium permanganate; sodium carbonate; In water; acetonitrile; at 20 - 70 ℃; for 1.5h;

DOI:10.1021/acs.joc.8b00655

upstream raw materials:

bornyl chloride

10,10-dinitro-bornan-2-ol

dl-camphene

Chloro<(1S)-7,7-dimethyl-2-oxobicyclo<2.2.1>hept-1-yl>sulfine

Downstream raw materials:

(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride

(1R)-7,7-dimethyl-1-phenylbicyclo<2.2.1>heptan-2-one

(1S,4R)-2-Hydroxy-7,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptane-1-carboxylic acid

(1S)-Ketopinoyl fluoride

Refernces

• 1、 Dalinger, Alexander I.,Kalinin, Mikhail A.,Kuranov, Sergey O.,Munkuev, Aldar A.,Okhina, Alina A.,Ottenbacher, Roman V.,Patrusheva, Oxana S.,Ponomarev, Konstantin Y.,Rogachev, Artem D.,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Vatsadze, Sergey Z.,Volcho, Konstantin P.. "Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones". . . Retrieved 2021/12/20.
• 2、 -. "NOVEL ARYLATED CAMPHENES, PROCESSES FOR THEIR PREPARATION AND USES THEREOF". Page/Page column 34. . Retrieved 2011/06/19.