Oblongolide

Base Information

• Chemical Name: Oblongolide
• CAS No.: 97344-05-3
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• DSSTox Substance ID: DTXSID00913964
• Nikkaji Number: J3.493.840G
• Wikidata: Q27107565
• Metabolomics Workbench ID: 68332
• ChEMBL ID: CHEMBL1077021

Synonyms:Oblongolide;Oblongolide A;97344-05-3;CHEBI:7715;CHEMBL1077021;C09519;(3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g][2]benzofuran-1-one;Naphtho[1,2-c]furan-1(3H)-one, 3a,5a,6,7,8,9,9a,9b-octahydro-7,9b-dimethyl-, (3aS,5aR,7S,9aS,9bR)-;AC1L428C;Naphtho(1,2-c)furan-1(3H)-one, 3a,5a,6,7,8,9,9a,9b-octahydro-7,9b-dimethyl-, (3aS,5aR,7S,9aS,9bR)-;DTXSID00913964;J3.493.840G;Q27107565;7,9b-dimethyl-3a,5a,6,7,8,9,9a,9b-octahydronaphtho[1,2-c]furan-1(3H)-one;(3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g]isobenzofuran-1-one;7beta,9balpha-Dimethyl-3aalpha,5aalpha,6,7,8,9,9abeta,9b-octahydronaphtho[1,2-c]furan-1(3H)-one

Chemical Property of Oblongolide

Chemical Property:

• Vapor Pressure: 7.05E-05mmHg at 25°C
• Boiling Point: 343.4°Cat760mmHg
• Flash Point: 142.7°C
• PSA: 26.30000
• Density: 1.057g/cm³
• LogP: 2.78790
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 220.146329876
• Heavy Atom Count: 16
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C1)C=CC3C2(C(=O)OC3)C
• Isomeric SMILES: C[C@H]1CC[C@H]2[C@H](C1)C=C[C@H]3[C@@]2(C(=O)OC3)C
• General Description: (3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-3a,5a,6,7,8,9,9a,9b-octahydronaphtho[1,2-c]furan-1(3H)-one, also known as (-)-oblongolide, is a norsesquiterpene lactone that can be synthesized efficiently through either an intramolecular Diels-Alder (IMDA) reaction or a transannular Diels-Alder (TDA) reaction. The TDA approach demonstrates superior stereoselectivity and yield, emphasizing the role of steric control in achieving the desired stereochemistry. (3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-3a,5a,6,7,8,9,9a,9b-octahydronaphtho[1,2-c]furan-1(3H)-one is derived from (-)-citronellol via key intermediates, highlighting its structural complexity and synthetic versatility.

Technology Process of Oblongolide

There total 5 articles about Oblongolide 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: 95.0%

(1S,2R,4aS,6R,8aR)-2-Hydroxymethyl-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid tert-butyl ester → oblongolide (97344-05-3)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 0.25h; Heating;

Reference yield:

tert-Butyl (2E,4E,10E)-(R)-(+)-2,6-dimethyl-12-hydroxyundeca-2,8,10-trienoate (168131-81-5) → oblongolide (97344-05-3) + oblongolide

Guidance literature:

With methylene blue; In tetrahydrofuran; 1,2-dichloro-benzene; at 210 ℃; for 76h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00123a011

Reference yield:

(1R,2R,4aS,6S,8aS)-2-Hydroxymethyl-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid tert-butyl ester → oblongolide (97344-05-3) + oblongolide

Guidance literature:

With methylene blue; In 1,2-dichloro-benzene; at 210 ℃; for 56h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00123a011

upstream raw materials:

(2E,8E,10E)-(S)-(+)-tert-butyl 2,6-dimethyl-12-hydroxy-dodeca-2,8,10-trienoate

tert-Butyl (2E,4E,10E)-(R)-(+)-2,6-dimethyl-12-hydroxyundeca-2,8,10-trienoate

Refernces

A Short Synthesis of Natural (-)-Oblongolide via an Intramolecular or a Transannular Diels-Alder Reaction

10.1021/jo00123a011

The study presents a concise synthesis of the natural product (-)-oblongolide, a norsesquiterpene lactone, using either an intramolecular Diels-Alder (IMDA) reaction or a transannular Diels-Alder (TDA) reaction as key steps. The synthesis begins with (-)-citronellol, which is transformed into a series of intermediates through various chemical reactions. Key intermediates include methyl (2E,4E,10E)-(S)-(+)-11-(tert-butoxycarbonyl)-7-methylundeca-2,4,10-trienoate (7), obtained via sequential Lemieux-Johnson oxidation, Wittig olefination, pyridinium dichromate oxidation, and Wadsworth-Emmons-Horner alkenation. A regioselective reduction of 7 yields tert-butyl (2E,8E,10E)-(S)-(+)-2,6-dimethyl-12-hydroxydodeca-2,8,10-trienoate (8), which then undergoes the IMDA reaction to form oblongolide (1). Alternatively, the macrocyclic lactone derived from 8 undergoes a TDA reaction to produce oblongolide with higher stereoselectivity and yield. The study highlights the importance of steric control in achieving the desired stereochemistry and the efficiency of the TDA reaction compared to the IMDA reaction.

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