Kolavenic acid

Base Information

• Chemical Name: Kolavenic acid
• CAS No.: 25436-90-2
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.473
• Nikkaji Number: J34.240H
• Wikidata: Q104397894
• Metabolomics Workbench ID: 123582
• ChEMBL ID: CHEMBL1517738
• Mol file: 25436-90-2.mol

Synonyms:kolavenic acid

Chemical Property of Kolavenic acid

Chemical Property:

• Vapor Pressure: 4.34E-08mmHg at 25°C
• Boiling Point: 416.1°C at 760 mmHg
• Flash Point: 310.8°C
• PSA: 37.30000
• Density: 0.968g/cm³
• LogP: 5.59630
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 304.240230259
• Heavy Atom Count: 22
• Complexity: 502

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C1(C)CCC(=CC(=O)O)C)CCC=C2C)C
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C/C(=O)O)/C)CCC=C2C)C

Technology Process of Kolavenic acid

There total 7 articles about Kolavenic 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:

(R)-(+)-3,4-dimethyl-2-cyclohexen-1-one (89162-97-0) → kolavenic acid (25436-90-2,25906-81-4)

Guidance literature:

Multi-step reaction with 7 steps

2: 2.) L-Selectride / 1.) benzene-toluene; 2.) THF

3: 1.) Me₂CHCMe₂BH₂, H₂O₂, NaOH; 2.) POCl₃ / 1.) THF; 2.) pyridine

5: 71 percent / dimethylsulfoxide

6: 31 percent / ZrCl2(η-C5H5)2

7: lithium hydroxide / 1,2-dimethoxy-ethane; H₂O / Ambient temperature

With lithium hydroxide; sodium hydroxide; Thexylboran; dihydrogen peroxide; L-Selectride; trichlorophosphate; zirconocene dichloride; In 1,2-dimethoxyethane; water; dimethyl sulfoxide;

DOI:10.1039/c39870000358

Reference yield:

(3R,4S,4aR,8aR)-3,4,8,8a-Tetramethyl-4-prop-2-ynyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene → kolavenic acid (25436-90-2,25906-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / ZrCl2(η-C5H5)2

2: lithium hydroxide / 1,2-dimethoxy-ethane; H₂O / Ambient temperature

With lithium hydroxide; zirconocene dichloride; In 1,2-dimethoxyethane; water;

DOI:10.1039/c39870000358

Reference yield:

(3R,4S,4aR,8aR)-4-(2-Bromo-ethyl)-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene (112358-88-0) → kolavenic acid (25436-90-2,25906-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / dimethylsulfoxide

2: 31 percent / ZrCl2(η-C5H5)2

3: lithium hydroxide / 1,2-dimethoxy-ethane; H₂O / Ambient temperature

With lithium hydroxide; zirconocene dichloride; In 1,2-dimethoxyethane; water; dimethyl sulfoxide;

DOI:10.1039/c39870000358

upstream raw materials:

kolavenic acid methyl ester

(R)-(+)-3,4-dimethyl-2-cyclohexen-1-one

(3R,4S,4aR,8aR)-4-(2-Bromo-ethyl)-3,4,8,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

(4aR,5S,6R)-5-ethenyl-4,4a,5,6,7,8-hexahydro-1,5,6-trimethyl-2(3H)-naphthalenone

Refernces