111025-83-3

Basic information

• Product Name: vinigrol
• Synonyms: vinigrol
• CAS NO: 111025-83-3
• Molecular Formula: C20H34O3
• Molecular Weight: 322.486
• Mol File: 111025-83-3.mol

Chemical Properties

• Boiling Point: 469.3°Cat760mmHg
• Flash Point: 209.7°C
• Appearance: /
• Density: 1.071g/cm³
• Vapor Pressure: 8.83E-11mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: vinigrol(CAS DataBase Reference)
• NIST Chemistry Reference: vinigrol(111025-83-3)
• EPA Substance Registry System: vinigrol(111025-83-3)

Safety Data

• Hazardous Substances Data: 111025-83-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H34O3/c1-11(2)15-7-5-12(3)17-9-14(10-21)19(22)18-16(15)8-6-13(4)20(17,18)23/h9,11-13,15-19,21-23H,5-8,10H2,1-4H3/t12-,13+,15-,16?,17-,18-,19+,20-/m0/s1

Related news

Efficient construction of 8-membered ring framework of vinigrol (cas 111025-83-3) through SmI2-induced coupling cyclization08/29/2019

The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI2-induced intramolecular coupling. It is particularly noteworthy that the 8-membered carbocycle was ...detailed

Stereoselective synthesis of the cis-decalin subunit of vinigrol (cas 111025-83-3) via three pericyclic reactions in cascade08/28/2019

Synthesis of the cis-decalin portion of vinigrol using a tandem oxy-Cope/Claisen/ene reaction is described. This three pericyclic reaction cascade proves to be a valuable synthetic tool in the construction of such systems.detailed

Chapter 1 - The Long and Winding Road of the vinigrol (cas 111025-83-3) Synthesis: A Learning Journey☆08/24/2019

Vinigrol is diterpene isolated from a fungus strain Virgaria nigra F-5408. Its tricyclic core comprises a cis-fused [4.4.0] system surmounted by a four-carbon bridge at C1 and C5 and features eight contiguous stereocenters. Biological testing of vinigrol has revealed a number of interesting prop...detailed

Relevant articles and documents

Asymmetric Total Synthesis of (-)-Vinigrol

A new strategy was developed for the asymmetric total synthesis of (-)-vinigrol. The strategy involved a linear sequence of 15 steps from 3-methyl-butanal (14 steps from chloro-dihydrocarvone) and did not need protecting groups. The synthetically challenging 1,5-butanodecahydronaphthalene core was constructed efficiently via a type II intramolecular [5+2] cycloaddition, followed by a unique ring-contraction cascade.

Synthesis method of vinigrol

The invention relates to a synthesis method of vinigrol. The synthesis method of the vinigrol comprises the following steps: by taking a synthesis starting point as a synthesis starting point, and carrying out a series of reactions such as an acylation reaction, an aromatization reaction, a bimolecular nucleophilic substitution reaction, a rearrangement reaction, an addition reaction, a hydroboration oxidation reaction, a ring shrinkage reaction and a redox reaction to obtain the vinigrol. The synthesis method of the vinigrol has the advantages of simpler synthesis route and fewer steps.

Method for asymmetrically synthesizing Vinigrol

The invention discloses a method for asymmetrically synthesizing Vinigrol. According to the method, a ten-membered carbocyclic compound is constructed through an oxy-Cope rearrangement reaction, and acascade reaction of trans-ring intramolecular Diels-Alder/CO2 removal is developed to obtain a Vingrol key cage-shaped skeleton structure; and in the subsequent synthesis of the Vingrol, the oxidation state adjustment of the key intermediate is realized through [4+2] reaction, reduction reaction and singlet oxygen oxidation reaction of singlet oxygen so as to complete the synthesis of the optically pure (-)-Vingrol. According to the invention, the method can also be used for synthesizing optically pure (+)-Vingrol and racemic (+/-)-Vingrol; and a plurality of Vinigrol analogues can also be obtained from the key intermediate after the Diels-Alder/CO2 removal reaction; and reaction operation in synthesis is simple, the method can be widely popularized and used, and sufficient samples are provided for activity testing.