Proximadiol

Base Information

• Chemical Name: Proximadiol
• CAS No.: 4666-84-6
• Deprecated CAS: 55353-16-7
• Molecular Formula: C₁₅H₂₈O₂
• Molecular Weight: 240.386
• UNII: Y2KBV9FZ9M
• DSSTox Substance ID: DTXSID001317282
• Nikkaji Number: J13.424D
• Wikidata: Q27136273
• Metabolomics Workbench ID: 136954
• ChEMBL ID: CHEMBL465860
• Mol file: 4666-84-6.mol

Synonyms:cryptomeridiol

Chemical Property of Proximadiol

Chemical Property:

• Vapor Pressure: 3.25E-05mmHg at 25°C
• Melting Point: 137.5 °C(Solv: benzene (71-43-2))
• Refractive Index: 1.506
• Boiling Point: 317.3 °C at 760 mmHg
• PKA: 15.18±0.60(Predicted)
• Flash Point: 137.3 °C
• PSA: 40.46000
• Density: 1.019g/cm³
• LogP: 3.11480
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 240.208930132
• Heavy Atom Count: 17
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

Cryptomeridiol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CC(CC2)C(C)(C)O)(C)O
• Isomeric SMILES: C[C@]12CCC[C@@]([C@@H]1C[C@@H](CC2)C(C)(C)O)(C)O
• Uses: Cryptomeridiol is a tyrosinase inhibitor from the leaves of Eucalyptus globulus. Terpenoid.

Technology Process of Proximadiol

There total 13 articles about Proximadiol 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: 100.0%

selin-11-en-4α-ol (37519-31-6) + methyllithium (917-54-4) → cryptomeridiol (60132-35-6,92857-25-5,108006-39-9,122674-21-9,143004-65-3,4666-84-6,55353-16-7)

Guidance literature:

selin-11-en-4α-ol; methyllithium; In diethyl ether; at -10 ℃; for 1h;

With hydrogenchloride; In diethyl ether; water;

DOI:10.1016/j.tetlet.2011.05.064

Reference yield: 81.0%

11-acetoxyeudesman-4α-ol → cryptomeridiol (60132-35-6,92857-25-5,108006-39-9,122674-21-9,143004-65-3,4666-84-6,55353-16-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.44.1603

Reference yield:

eudesobovatol A (125196-77-2) → cryptomeridiol (60132-35-6,92857-25-5,108006-39-9,122674-21-9,143004-65-3,4666-84-6,55353-16-7) + obovatol (83864-78-2)

Guidance literature:

With trifluoroacetic acid; In benzene;

DOI:10.1016/S0040-4039(01)93502-6

upstream raw materials:

elemol

eudesmagnolol

eudeshonokiol A

2-[(2R,4aR,8R,8aR)-8-(3,5'-Diallyl-2'-methoxy-biphenyl-4-yloxy)-4a,8-dimethyl-decahydro-naphthalen-2-yl]-propan-2-ol

Refernces

A Short-Step Synthetic Approach to Eudesmane Skeleton. A Synthesis of (+/-)-β-Eudesmol and Related Eudesman Sesquiterpenes

10.1246/bcsj.61.3770

The research aims to develop an efficient and concise method for synthesizing the eudesmane skeleton, which is a significant structural motif in various sesquiterpenes, including (±)-β-eudesmol, cryptomeridiol, and neointermediol. The study employs a strategy based on the use of key intermediates like A or B, which undergo intramolecular cyclization via aldol condensation or Michael reaction. The synthesis starts from readily available 3-vinyl-2-cyclohexen-1-one, which is treated with dimethyl malonate in the presence of sodium methoxide to yield the Michael adduct. Subsequent steps involve acetalization, reduction with lithium aluminum hydride, selective benzylation, oxidation with pyridinium dichromate (PDC), and catalytic hydrogenation. The crucial step is the intramolecular aldol condensation, which constructs the desired α,β-unsaturated ketone. The final steps include oxidation, esterification, and selective reduction to obtain the target compounds. The research concludes that this approach provides a general method for constructing eudesmane sesquiterpenes, offering a formal total synthesis of (±)-β-eudesmol and its related compounds.

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