pinolidoxin

Base Information

• Chemical Name: pinolidoxin
• CAS No.: 152985-39-2
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401
• Mol file: 152985-39-2.mol

Synonyms:2H-Oxecin,2,4-hexadienoic acid deriv.; (+)-Lethaloxin; (+)-Pinolidoxin; Lethaloxin;Pinolidoxin

Chemical Property of pinolidoxin

Chemical Property:

• Vapor Pressure: 1.35E-12mmHg at 25°C
• Boiling Point: 511.4°Cat760mmHg
• Flash Point: 178.8°C
• PSA: 93.06000
• Density: 1.16g/cm³
• LogP: 1.81420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of pinolidoxin

There total 15 articles about pinolidoxin 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%

hexa-2,4-dienoic acid 2,2-dimethyl-6-oxo-4-propyl-3a,6,7,8,9,11a-hexahydro-4H-1,3,5-trioxa-cyclopentacyclodecen-7-yl ester (443309-11-3) → (-)-pinolidoxin (152985-39-2)

Guidance literature:

With hydrogenchloride; In methanol; at 65 ℃;

DOI:10.1021/ja020238i

Reference yield: 95.0%

(2E,4E)-Hexa-2,4-dienoic acid (E)-(3aS,4S,11aR)-2,2-dimethyl-6-oxo-4-propyl-3a,6,7,8,9,11a-hexahydro-4H-1,3,5-trioxa-cyclopentacyclodecen-7-yl ester → (-)-pinolidoxin (152985-39-2)

Guidance literature:

With hydrogenchloride; In methanol; at 65 ℃; for 1.25h;

DOI:10.1021/ja020238i

Reference yield: 81.0%

(2E,4E)-Hexa-2,4-dienoic acid (E)-(3aR,4R,7S,11aS)-2,2-dimethyl-6-oxo-4-propyl-3a,6,7,8,9,11a-hexahydro-4H-1,3,5-trioxa-cyclopentacyclodecen-7-yl ester (245420-84-2) → pinolidoxin (152985-39-2)

Guidance literature:

With ethandithiol; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo051353p

upstream raw materials:

hexa-2,4-dienoic acid 2,2-dimethyl-6-oxo-4-propyl-3a,6,7,8,9,11a-hexahydro-4H-1,3,5-trioxa-cyclopentacyclodecen-7-yl ester

(2E,4E)-Hexa-2,4-dienoic acid (R)-1-((1S,2R,3R)-2,3-dihydroxy-1-propyl-pent-4-enyloxycarbonyl)-pent-4-enyl ester

sorbic Acid

(S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)butan-1-ol

Refernces

• 1、 Garcia-Fortanet, Jorge,Murga, Juan,Falomir, Eva,Carda, Miguel,Marco, J. Alberto. "Stereoselective total synthesis and absolute configuration of the natural decanolides (-)-microcarpalide and (+)-lethaloxin. Identity of (+)-lethaloxin and (+)-pinolidoxin". . p. 9822 - 9827. Retrieved 2007/10/03.
• 2、 Liu, Dong,Kozmin, Sergey A.. "Synthesis of (-)-pinolidoxin: Divergent synthetic strategy exploiting a common silacyclic precursor". . p. 3005 - 3007. Retrieved 2007/10/03.