Vitispirane

Base Information

• Chemical Name: Vitispirane
• CAS No.: 65416-59-3
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.301
• DSSTox Substance ID: DTXSID80867153
• Nikkaji Number: J20.178B
• Wikidata: Q81986486
• Metabolomics Workbench ID: 47518
• Mol file: 65416-59-3.mol

Synonyms:Damascones;Ionone;Ionones;Irone;Irones;Megastigmanes;Nor Isoprenoid;Nor Isoprenoids;Nor-Isoprenoid;Nor-Isoprenoids;Norisoprenoid;Norisoprenoids;Theaspiranes;Vitispirane;Vitispiranes

Chemical Property of Vitispirane

Chemical Property:

• Vapor Pressure: 0.0218mmHg at 25°C
• Boiling Point: 258.7°C at 760 mmHg
• Flash Point: 106.7°C
• PSA: 9.23000
• Density: 0.95g/cm³
• LogP: 3.46640
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 288

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(O1)C(=C)C=CCC2(C)C

Technology Process of Vitispirane

There total 21 articles about Vitispirane 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: 84.0%

(2RS,7RS)-2,10,10-trimethyl-6-methylidene-1-oxaspiro<4.5>decan-7-ol → (2RS,5RS)-vitispirane (65416-59-3,66965-94-4,66965-95-5,99881-85-3,99944-79-3,116296-76-5,116296-77-6)

Guidance literature:

(2RS,7RS)-2,10,10-trimethyl-6-methylidene-1-oxaspiro<4.5>decan-7-ol; With pyridine; acetic anhydride; at 20 ℃; for 24h; Inert atmosphere;

With palladium diacetate; triphenylphosphine; calcium carbonate; In 1,4-dioxane; for 6.5h; Reflux; Inert atmosphere;

DOI:10.3762/bjoc.9.262

Reference yield: 24.0%

3',4'-dehydro-1',2'-dihydroxy-2',3',3,4-tetrahydro-α-ionol → 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-ene (65416-59-3,256651-64-6) + (2S,5S,6R)-2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-7-en-6-ol + (2R,5S,6R)-2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-7-en-6-ol

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; for 2h; Heating;

Reference yield:

6,9-dihydroxymegastigma-4,7-dien-3-one (23526-45-6,24427-77-8,50763-72-9,50763-73-0) → 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-ene (65416-59-3,256651-64-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 47 percent / 6 N NaOH, 30percent H₂O₂ / methanol

2: 50 percent / H₂ / platinum oxide / ethyl acetate / Ambient temperature

3: 44 percent / 80percent hydrazine hydrate / methanol

4: 10 percent / tosyl chloride, pyridine / 2 h / Heating

With pyridine; sodium hydroxide; hydrogen; dihydrogen peroxide; hydrazine hydrate; p-toluenesulfonyl chloride; platinum(IV) oxide; In methanol; ethyl acetate;

upstream raw materials:

6,6-dimethyl-2-methylene-1-(3-oxobutyl)-3-cyclohexen-1-ol

7,8-dihydro-3,4-dehydro-β-ionol

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one

6,6-dimethyl-2-methylene-1-(3-oxo-1-butenyl)-3-cyclohexen-1-ol

Refernces

• 1、 Nilsson, Ylva I. M.,Aranyos, Attila,Andersson, Pher G.,Baeckvall, Jan-E.,Parrain, Jean-Luc,Ploteau, Christelle,Quintard, Jean-Paul. "Syntheses of theaspirone and vitispirane via palladium(II)-catalyzed oxaspirocyclization". . p. 1825 - 1829. Retrieved 2007/10/03.
• 2、 Etoh, Hideo,Ina, Kazuo,Iguchi, Masanobu. "New Syntheses of Edulans and Theaspiranes from α-Inone". . p. 2871 - 2876. Retrieved 2007/10/02.