Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI)

Base Information

• Chemical Name: Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI)
• CAS No.: 716381-20-3
• Molecular Formula: C12H16 O4
• Molecular Weight: 224.25304
• Mol file: 716381-20-3.mol

Synonyms:Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI)

Chemical Property of Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI)

Chemical Property:

• PSA: 63.60000
• LogP: 0.97990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI)

There total 3 articles about Spiro[2.5]oct-4-ene-5-carboxylic acid, 8-hydroxy-4,8-dimethyl-6-oxo-, methyl ester (9CI) 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: 72.0%

1,1-diacetylcyclopropane (695-70-5) + acetoacetic acid methyl ester (105-45-3) → 8-hydroxy-4,8-dimethyl-6-oxo-spiro[2.5]oct-4-ene-5-carboxylic acid methyl ester (716381-20-3)

Guidance literature:

acetoacetic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

1,1-diacetylcyclopropane; In tetrahydrofuran; at -78 - 20 ℃; for 14h;

DOI:10.1016/j.bmc.2006.03.037

Reference yield: 71.0%

1,1-diacetylcyclopropane (695-70-5) + Chan's diene (81114-98-9) → 8-hydroxy-4,8-dimethyl-6-oxo-spiro[2.5]oct-4-ene-5-carboxylic acid methyl ester (716381-20-3)

Guidance literature:

With 4 A molecular sieve; titanium tetrachloride; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2006.03.037

Reference yield: 55.0%

1,1-diacetylcyclopropane (695-70-5) + 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1,81114-98-9,67609-52-3) → 8-hydroxy-4,8-dimethyl-6-oxo-spiro[2.5]oct-4-ene-5-carboxylic acid methyl ester (716381-20-3)

Guidance literature:

With 4 A molecular sieve; titanium tetrachloride; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/anie.200351263

upstream raw materials:

1,1-diacetylcyclopropane

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

acetoacetic acid methyl ester

Chan's diene

Downstream raw materials:

methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate

Refernces

• 1、 Bose, Gopal,Bracht, Karin,Bednarski, Patrick J.,Lalk, Michael,Langer, Peter. "Synthesis, reactions and structure-activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity". . p. 4694 - 4703. Retrieved 2007/10/03.