2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

Base Information

• Chemical Name: 2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid
• CAS No.: 3650-43-9
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Hs Code.: 2916209090
• Wikidata: Q105274103
• Mol file: 3650-43-9.mol

Synonyms:beta-Costic acid;2-(4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid;b-Costic acid;4(15),11(13)-Selinadien-12-oic acid

Chemical Property of 2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

Chemical Property:

• Vapor Pressure: 2.96E-06mmHg at 25°C
• Melting Point: 87-88℃
• Boiling Point: 362.9°C at 760 mmHg
• PKA: 4.42±0.11(Predicted)
• Flash Point: 263.8°C
• PSA: 37.30000
• Density: 1.04g/cm³
• LogP: 3.78990
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 369

Purity/Quality:

99% ^*data from raw suppliers

β-Costicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(=C)C1CC(CC2)C(=C)C(=O)O
• Uses: Costic Acid is an impurity of Eudesmane(CAS#: 473-11-0 ); it is a refrigerant compound comprising Iodotrifluoromethane and stabilizers.

Technology Process of 2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

There total 9 articles about 2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic 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:

germacra-1(10),4,11(13)-trien-12-oic acid (347377-92-8) → β-costic acid (3650-43-9) + 2-((2R,4aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl)acrylic acid (69978-82-1,62458-44-0) + (+)-Eudesma-3,11(13)-dien-12-oic acid (28399-17-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 0.116667h;

DOI:10.1016/S0031-9422(01)00291-6

Reference yield:

dl-β-costal (3650-40-6,76497-23-9,88564-53-8) → (+/-)-Cortysaeure (3650-43-9,122674-23-1)

Guidance literature:

With sodium hydroxide; silver nitrate;

DOI:10.1021/jo01347a045

Reference yield:

Methanesulfonic acid (2S,4aR,8aS)-4a-methyl-8-methylene-decahydro-naphthalen-2-yl ester (4966-46-5) → (+/-)-Cortysaeure (3650-43-9,122674-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH

2: (i) NaH, (ii) LiAlH₄, (iii) MnO₂

3: AgNO₃, aq. NaOH

With sodium hydroxide; sodium hydride; silver nitrate;

DOI:10.1021/jo01347a045

upstream raw materials:

germacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-12-oic acid

dl-β-costal

Methanesulfonic acid (2S,4aR,8aS)-4a-methyl-8-methylene-decahydro-naphthalen-2-yl ester

Refernces

• 1、 Herz et al.. "". . p. 1632. Retrieved 1966.
• 2、 Marshall,Pike,Carroll. "Studies leading to the stereoselective total synthesis of dl-beta-eudesmol, dl-beta-selinene, dl-costol, and related naturally occurring sesquiterpenes.". . p. 2933 - 2941. Retrieved 2007/10/10.