Neoisoverbanol

Base Information

• Chemical Name: Neoisoverbanol
• CAS No.: 473-64-3
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Mol file: 473-64-3.mol

Synonyms:neoisoverbanol;(+)-Neoisoverbanol;(1R,2R,4S,5R)-4,6,6-Trimethyl-bicyclo[3.1.1]heptan-2-ol;(1R:2S:4R)-Pinanol-(4);Neo-isoverbanol;(1R-(1α,2α,4α,5α))-4,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol;

Chemical Property of Neoisoverbanol

Chemical Property:

• PSA: 20.23000
• LogP: 2.04940

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Neoisoverbanol

There total 2 articles about Neoisoverbanol 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:

2,6,6-trimethylbicyclo[3.1.1]heptane (473-55-2,4755-33-3,4795-86-2,4863-59-6,6876-13-7,10281-53-5,33626-25-4,112456-46-9,112456-47-0) → (1R*,2R*,3R*,5S*)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (51152-11-5) + iso-pinocamphone (473-62-1,547-60-4,14575-93-0,15358-88-0,18358-53-7,18492-59-6,22339-21-5,30469-22-8,30517-87-4) + pinan-2α-ol (473-54-1,4948-28-1,4948-29-2,18492-55-2,23516-36-1,25926-77-6,35408-04-9,35519-42-7,112574-21-7) + isoverbanol (473-64-3,473-65-4,515-88-8,7316-84-9,24739-64-8,35997-97-8,39166-53-5,39776-66-4,73307-11-6,94480-80-5,94480-81-6,94480-82-7,94480-83-8) + 1-acetyl-2,2-dimethyl-3-ethylcyclobutane (4951-97-7,67465-27-4) + cis-pinane-2-ol (473-54-1,4948-28-1,4948-29-2,18492-55-2,23516-36-1,25926-77-6,35408-04-9,35519-42-7,112574-21-7)

Guidance literature:

With oxygen; sodium sulfite; Product distribution; Mechanism; 1.) 70 deg C, 34 h, 2.) H₂O, 60 deg C, 4 h; other trans-pinane; var. temps.;

DOI:10.1002/prac.19923340506

Reference yield:

Verbenone (18309-32-5) → (1R,5R)-4,6,6-Trimethyl-bicyclo[3.1.1]heptan-2-ol (473-64-3,473-65-4,515-88-8,7316-84-9,24739-64-8,35997-97-8,39166-53-5,39776-66-4,73307-11-6,94480-80-5,94480-81-6,94480-82-7,94480-83-8) + (1R,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol (473-67-6,1820-09-3,1845-30-3,5416-53-5,13040-03-4,18881-04-4,19890-02-9,22339-08-8,80795-83-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1039/c2gc35619h

Reference yield:

(1R,2S,4R,5R)-(+)-neoisoverbanol (473-64-3) → (1R)-(+)-cis-pinane (4795-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; toluene / thermische Zersetzung des gebildeten Xanthogensaeure-methylesters

2: Raney nickel; diethyl ether / 90 - 100 °C / 44130.5 Torr / Hydrogenation

With diethyl ether; nickel; toluene;

upstream raw materials:

Verbenone

2,6,6-trimethylbicyclo[3.1.1]heptane

Downstream raw materials:

(1R)-(+)-cis-pinane

Refernces

• 1、 Brose, Thomas,Pritzkow, Wilhelm,Thomas, Gerda. "Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen". . p. 403 - 409. Retrieved 2007/10/02.