Pinusolide

Base Information

• Chemical Name: Pinusolide
• CAS No.: 31685-80-0
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• DSSTox Substance ID: DTXSID90953637
• Nikkaji Number: J17.758J
• Wikidata: Q27137577
• ChEMBL ID: CHEMBL425068
• Mol file: 31685-80-0.mol

Synonyms:pinusolide

Chemical Property of Pinusolide

Chemical Property:

• Vapor Pressure: 7.76E-09mmHg at 25°C
• Melting Point: 82-84 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 465.3°Cat760mmHg
• Flash Point: 228.5°C
• PSA: 52.60000
• Density: 1.1g/cm³
• LogP: 4.20170
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 346.21440943
• Heavy Atom Count: 25
• Complexity: 619

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pinusolide >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC(=C)C2CCC3=CCOC3=O)(C)C(=O)OC
• Isomeric SMILES: C[C@]12CCC[C@]([C@@H]1CCC(=C)[C@@H]2CCC3=CCOC3=O)(C)C(=O)OC

Technology Process of Pinusolide

There total 6 articles about Pinusolide 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: 67.0%

methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate (909297-15-0) → Pinusolide (31685-80-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.5h;

DOI:10.1134/S1070428006060030

Reference yield:

methanol (67-56-1) + lambertianic acid methyl ester (1238-98-8,2222-52-8,4966-14-7,10267-15-9) → Pinusolide (31685-80-0)

Guidance literature:

methanol; lambertianic acid methyl ester; With chloramine-B; acetic acid; at 5 ℃; for 0.5h;

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2006.05.077

Reference yield:

lambertiainic acid (1235-76-3,1235-77-4,4966-13-6,10267-14-8) → Pinusolide (31685-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / diethyl ether / 2 h / 20 °C

2.1: N-chlorobenzenesulfonamide sodium salt; acetic acid / 0.5 h / 5 °C

2.2: 1.18 g / aq. HCl / dioxane / 0.5 h / 20 °C

With chloramine-B; acetic acid; In diethyl ether;

DOI:10.1016/j.bmcl.2006.05.077

upstream raw materials:

diazomethane

methyl 5-[2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalene-1-carboxylate

methanol

lambertianic acid methyl ester

Downstream raw materials:

lambertianic acid methyl ester

Refernces

• 1、 Chernov,Shul'ts,Shakirov,Tolstikov. "Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid". . p. 828 - 838. Retrieved 2007/10/03.