Methyl trans-communate

Base Information

• Chemical Name: Methyl trans-communate
• CAS No.: 15798-13-7
• Molecular Formula: C21H32O2
• Molecular Weight: 316.484
• UNII: P8PD6BRA3K
• Nikkaji Number: J129.776G,J139.854G,J108.427E
• Wikidata: Q104375917
• Mol file: 15798-13-7.mol

Synonyms:Methyl trans-communate;Methyl communate, (E)-;P8PD6BRA3K;15798-13-7;trans-Communic acid methyl ester;UNII-P8PD6BRA3K;Labda-8(20),12,14-trien-19-oic acid, methyl ester, (E)-;Methyl (E)-8(20),12,14-labdatrien-19-oate;Methyl cis-Communate;1235-39-8;1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-((2E)-3-methyl-2,4-pentadien-1-yl)-, methyl ester, (1S,4aR,5S,8aR)-;(12E)-Labda-8(17),12,14-triene-19-oic acid methyl ester;10178-35-5;(1S,8aalpha)-1,4abeta-Dimethyl-5beta-(3-methyl-2,4-pentadienyl)-6-methylenedecalin-1beta-carboxylic acid methyl e;methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate;1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-(3-methyl-2,4-pentadienyl)-, methyl ester, [1S-[1.alpha.,4a.alpha.,5.alpha.(Z),8a.beta.]]-;Labda-8(20),12,14-trien-19-oic acid methyl ester;Labda-8(20),12,14-trien-19-oic acid, methyl ester;1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-(3-methyl-2,4-pentadienyl)-, methyl ester, [1S-(1.alpha.,4a.alpha.,5.alpha.,8a.beta.)]-;1-Naphthalenecarboxylic acid, decahydro-1,4a-dimethyl-6-methylene-5-(3-methyl-2,4-pentadienyl)-, methyl ester, [1S-[1.alpha.,4a.alpha.,5.alpha.(E),8a.beta.]]-

Chemical Property of Methyl trans-communate

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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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 Methyl trans-communate

There total 7 articles about Methyl trans-communate 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: 97.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-communic acid (1231-35-2,2761-77-5,5573-13-7,53109-43-6,60872-81-3,67710-87-6,69427-96-9,83945-57-7,10178-32-2) → (E)-methyl communate (15798-13-7)

Guidance literature:

In diethyl ether; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2007-985586

Reference yield: 95.0%

(E)-communic acid (1231-35-2,2761-77-5,5573-13-7,53109-43-6,60872-81-3,67710-87-6,69427-96-9,83945-57-7,10178-32-2) + methyl iodide (74-88-4) → (E)-methyl communate (15798-13-7)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1002/anie.201208412

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

upstream raw materials:

diazomethane

(E)-communic acid

methyl iodide

methyl communate ester

Downstream raw materials:

1β-<2-Methyl-5,5,6,6-tetracyan-cyclohexen-(2)-yl-(1)-methyl>-2-methylen-5β-methoxycarbonyl-5α,9β-dimethyl-trans-dekalin

trans-communol

Communol

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

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.