1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-

Base Information

• Chemical Name: 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-
• CAS No.: 10178-35-5
• Molecular Formula: C21H32O2
• Molecular Weight: 316.484
• UNII: AB66XA2NG9
• Mol file: 10178-35-5.mol

Synonyms:Methyl elliotinoate;Methyl cis-Communate;Methyl (Z)-communate;Methyl communate, (Z)-;AB66XA2NG9;UNII-AB66XA2NG9;1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-;10178-35-5;(12Z)-Labda-8(17),12,14-triene-19-oic acid methyl ester;Labda-8(20),12,14-trien-19-oic acid, methyl ester, (Z)-

Chemical Property of 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-

Chemical Property:

• PSA: 26.30000
• LogP: 5.46070
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 530

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1C(=C)CCC2C1(CCCC2(C)C(=O)OC)C)C=C
• Isomeric SMILES: C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)OC)C)/C=C

Technology Process of 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-

There total 6 articles about 1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2Z)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)- 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: 74.0%

methyl communate ester (1235-39-8) → (E)-methyl communate (15798-13-7) + methyl ester of cis-communic acid (10178-35-5)

Guidance literature:

With iodine; In cyclohexane; at 90 ℃; for 2h; Overall yield = 300 mg; Inert atmosphere;

DOI:10.1002/anie.201208412

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + cis-communic acid (1231-35-2,2761-77-5,5573-13-7,10178-32-2,53109-43-6,60872-81-3,67710-87-6,69427-96-9,83945-57-7) → cis-communic acid (1235-39-8,10178-35-5,15798-13-7,19533-84-7,52992-94-6,67710-86-5,69427-97-0,70224-44-1,114674-21-4,148153-41-7,148153-42-8)

Guidance literature:

DOI:10.1248/cpb.36.3967

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (Z)-labda-8(17),12,14-trien-19-oic acid (2761-77-5,5573-13-7,10178-32-2,53109-43-6,60872-81-3,67710-87-6,69427-96-9,83945-57-7,1231-35-2) → methyl ester of cis-communic acid (10178-35-5)

Guidance literature:

upstream raw materials:

diazomethane

(Z)-labda-8⁽¹⁷⁾,12,14-trien-19-oic acid

methyl communate ester

cis-communic acid

Downstream raw materials:

Communol

12,19-dihydrox-13,14,15,16-tetranorlabd-8⁽¹⁷⁾-ene

cis-communol

(-)-ambroxide

Refernces

13C NMR Data for Labdane Diterpenoids

10.1002/mrc.1260310317

The research aims to provide a comprehensive analysis of the 13C NMR spectra of 91 labdane-type diterpenoid compounds, categorized into ten different series. The purpose of this study was to fill the gap in the literature regarding the compilation of 13C NMR data for labdane-type compounds, which could serve as models for the assignment of similar compounds in future research. Through the analysis of the 13C NMR spectra, the researchers observed consistent chemical shifts for the decalin system across various compounds and noted significant changes in chemical shifts when the side-chain contained oxygenated groups or double bonds in specific positions. The study utilized various labdane diterpenoids, including methyl mirceocommunate, methyl trans-communate, methyl cis-communate, and cis-abienol, which were subjected to reactions such as ozonolysis, oxymercuration-demercuration, hydroboration-oxidation, hydrogenation, epoxidation, and photooxidation to derive the compounds for analysis. The conclusions drawn from this research offer valuable insights into the structural elucidation of labdane-type compounds and contribute to the understanding of their NMR spectral characteristics.