Lupane

Base Information

• Chemical Name: Lupane
• CAS No.: 464-99-3
• Molecular Formula: C₃₀H₅₂
• Molecular Weight: 412.743
• Nikkaji Number: J39.887J
• Metabolomics Workbench ID: 55390
• Mol file: 464-99-3.mol

Synonyms:lupane

Chemical Property of Lupane

Chemical Property:

• Vapor Pressure: 4.06E-08mmHg at 25°C
• Boiling Point: 457.4°Cat760mmHg
• Flash Point: 221.8°C
• PSA: 0.00000
• Density: 0.925g/cm³
• LogP: 9.13390
• XLogP3: 11.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 412.406901659
• Heavy Atom Count: 30
• Complexity: 688

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC2(C1C3CCC4C5(CCCC(C5CCC4(C3(CC2)C)C)(C)C)C)C
• Isomeric SMILES: CC(C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CCCC([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)C)C

Technology Process of Lupane

There total 21 articles about Lupane 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: 56.0%

3-Oxo-28-lupanal (54145-78-7) → Lupane (464-99-3)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; In diethylene glycol; 1.) 100 deg C, 1 h, 2.) 200-210 deg C, 4 h;

Reference yield:

α-lupene (1721-81-9) → lupane (464-99-3)

Guidance literature:

With ethyl acetate; platinum; at 40 ℃; Hydrogenation;

Reference yield:

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol (1072913-62-2) → Lupane (464-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 2 h / 1520 Torr

2: 87.8 percent / pyridinium chlorochromate / CH₂Cl₂

3: 56 percent / 85 percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 1.) 100 deg C, 1 h, 2.) 200-210 deg C, 4 h

With potassium hydroxide; hydrogen; hydrazine hydrate; pyridinium chlorochromate; palladium on activated charcoal; In dichloromethane; ethyl acetate; diethylene glycol;

upstream raw materials:

lupan-3-one

lupan-2⁽³⁾-ene

α-lupene

lup-2-en-1-one

Refernces

UNEXPECTED REGIOSPECIFICITY IN PHOTOCHEMICAL α-CLEAVAGE OF HYDRINDANONES.

10.1016/S0040-4039(01)91553-9

The research investigates the unexpected regiospecificity in the photochemical α-cleavage of hydrindanones derived from triterpenes. The study focuses on the photolysis of trans- and cis-hydrindanones, specifically compounds like 22,29,30-trinorhopan-21-one and 22,29,30-trinor-(17aH)-hopan-21-one in the hopane series, and analogous compounds in the lupane series. The trans-hydrindanones were found to cleave predominantly on the least substituted side of the carbonyl group, yielding unsaturated aldehydes, while the cis-hydrindanones cleaved on the more highly substituted side, resulting in methyl esters. The regiospecificity was shown to be strictly stereochemistry-dependent. The chemicals involved in the research include the starting materials such as hopane and lupane precursors, solvents like degassed anhydrous methanol, and the reaction products like unsaturated aldehydes and methyl esters. The study utilized techniques such as capillary gas chromatography and GC-mass spectrometry for analysis. The findings suggest that pure compounds can be obtained in high yields through this photoinduced cleavage, which could have synthetic applications. Further investigations into the kinetic aspects and quantum efficiencies of these reactions are proposed to elucidate the underlying mechanisms.

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