7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride

Base Information

• Chemical Name: 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride
• CAS No.: 54371-12-9
• Molecular Formula: C10H13ClO2
• Molecular Weight: 200.665
• DSSTox Substance ID: DTXSID70510126
• Nikkaji Number: J2.109.997J
• Mol file: 54371-12-9.mol

Synonyms:54371-12-9;7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride;DTXSID70510126;AKOS024330189;EN300-370455;7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonylchloride

Chemical Property of 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride

Chemical Property:

• PSA: 34.14000
• LogP: 2.14720
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 200.0604073
• Heavy Atom Count: 13
• Complexity: 295

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(=O)C2)C(=O)Cl)C

Technology Process of 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride

There total 12 articles about 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbonyl chloride 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: 96.0%

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) → ketopinic acid chloride (54371-12-9,66884-33-1,66965-39-7,86023-72-5)

Guidance literature:

With pyridine; thionyl chloride; for 2h; Reflux;

DOI:10.1021/acs.joc.8b00655

Reference yield:

(1S)-10-camphorsulfonic acid (3144-16-9,61380-66-3) → ketopinic acid chloride (54371-12-9,66884-33-1,66965-39-7,86023-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / SOCl₂

2: 30 percent / KMnO₄

3: SOCl₂

With potassium permanganate; thionyl chloride;

DOI:10.1051/jcp/1996930575

Reference yield:

Camphorsulfonyl chloride (21286-54-4) → ketopinic acid chloride (54371-12-9,66884-33-1,66965-39-7,86023-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / KMnO₄

2: SOCl₂

With potassium permanganate; thionyl chloride;

DOI:10.1051/jcp/1996930575

upstream raw materials:

ketopinic acid

(1S)-ketopinic acid

(1S)-(+)-ketopinic acid

(1S,2R)-7,7-dimethyl-2-methoxybicyclo[2.2.1]heptane-1-carboxylic acid chloride

Downstream raw materials:

(1S,2R,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-o

(1S,2R,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-ol

(1S,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one

(1S,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one

Refernces

• 1、 Lee, Dong-Sheng. "Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation". . p. 2014 - 2020. Retrieved 2009.
• 2、 Hemmersbach, Lars,Romanski, Steffen,Botov, Svetlana,Adler, Andreas,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "On the Diastereoselectivity of the Complexation of Ketopinic Acid-Derived 2-Acyloxy-1,3-cyclohexadienes and the Configurational Stability of Dienol-Fe(CO)3Complexes. A Case Study". supporting information. p. 2909 - 2914. Retrieved 2021/08/30.
• 3、 Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.. "Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones". . p. 12951 - 12964. Retrieved 2018/11/30.