9alpha,11-Dihydroxydrim-7-en-6-one

Base Information

• Chemical Name: 9alpha,11-Dihydroxydrim-7-en-6-one
• CAS No.: 127681-58-7
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• ChEMBL ID: CHEMBL1900011
• DSSTox Substance ID: DTXSID201347667
• Nikkaji Number: J747.497K
• Wikidata: Q104962047
• Mol file: 127681-58-7.mol

Synonyms:9alpha,11-Dihydroxydrim-7-en-6-one;127681-58-7;(4R,4aS,8aS)-4-hydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydronaphthalen-1-one;9|A,11-Dihydroxydrim-7-en-6-one;MLS000876786;MEGxm0_000034;CHEMBL1900011;ACon0_000569;ACon1_001303;DTXSID201347667;HMS2270I14;AKOS040761302;NCGC00180650-01;NCGC00180650-02;SMR000440589;NS00097238;BRD-K54975600-001-01-5

Chemical Property of 9alpha,11-Dihydroxydrim-7-en-6-one

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 252.17254462
• Heavy Atom Count: 18
• Complexity: 410

Purity/Quality:

98.0% ^*data from raw suppliers

9α,11-Dihydroxydrim-7-en-6-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C2C(CCCC2(C1(CO)O)C)(C)C
• Isomeric SMILES: CC1=CC(=O)[C@@H]2[C@@]([C@]1(CO)O)(CCCC2(C)C)C

Technology Process of 9alpha,11-Dihydroxydrim-7-en-6-one

There total 14 articles about 9alpha,11-Dihydroxydrim-7-en-6-one 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: 90.0%

(4aS,8aS)-3,4a,8,8-Tetramethyl-4-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one (127681-57-6) → (4R,4aS,8aS)-4-Hydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one (127681-58-7)

Guidance literature:

With pyridine; osmium(VIII) oxide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1080/14786419.2012.706297

Reference yield:

C15H22O2 → (4R,4aS,8aS)-4-Hydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one (127681-58-7)

Guidance literature:

With perchloric acid; In tetrahydrofuran; at 20 ℃; for 49h;

DOI:10.1080/14786419.2012.706297

Reference yield:

((1S,4aS,8aR)-2,5,5,8a-Tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl acetate (110547-82-5) → (4R,4aS,8aS)-4-Hydroxy-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one (127681-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / DBU / benzene / 3.5 h / Heating

2: 88 percent / OsO₄; pyridine / 2-methyl-propan-2-ol / 20 °C

With pyridine; osmium(VIII) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tert-butyl alcohol; benzene; 1: Elimination / 2: Addition;

DOI:10.1055/s-2000-8225

upstream raw materials:

7,9-drimadien-6-one

6-oxo-7-drimen-11-ol acetate

6-oxo-7-drimen-11-ol

(+)-uvidin A

Downstream raw materials:

(-)-cinnamodial

(-)-epi-Albrassitriol

(-)-Albrassitriol

(5S,6S)-5-hydroxy-4,5-di(hydroxymethyl)-6,10,10-trimethylbicyclo[4.4.0]dec-3-en-2-one