(5S)-bicyclo[3.3.1]nonane-2,6-dione

Base Information

• Chemical Name: (5S)-bicyclo[3.3.1]nonane-2,6-dione
• CAS No.: 36415-87-9
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• DSSTox Substance ID: DTXSID10351914
• Mol file: 36415-87-9.mol

Synonyms:36415-87-9;CTK1B6321;DTXSID10351914

Chemical Property of (5S)-bicyclo[3.3.1]nonane-2,6-dione

Chemical Property:

• PSA: 34.14000
• LogP: 1.33470
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C2CCC(=O)C1C2
• Isomeric SMILES: C1CC(=O)C2CCC(=O)[C@@H]1C2

Technology Process of (5S)-bicyclo[3.3.1]nonane-2,6-dione

There total 15 articles about (5S)-bicyclo[3.3.1]nonane-2,6-dione 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: 59.0%

bicyclo[3.3.1]nonane-2,6-dione (16473-11-3) → (S,S)-bicyclo[3.3.1]nonane-2,6-dione (36415-87-9)

Guidance literature:

With baker's yeast; Sucrose; In water; at 36 - 38 ℃; for 288h; Enzymatic reaction;

DOI:10.1002/ejoc.200700241

Reference yield: 48.0%

bicyclo[3.3.1]nonane-2,6-dione (16473-11-3) → 6-hydroxybicyclo[3.3.1]nonan-2-one (1092543-24-2) + (S,S)-bicyclo[3.3.1]nonane-2,6-dione (36415-87-9) + (1S,5S)-6-hydroxy-bicyclo[3.3.1]nonan-2-one

Guidance literature:

With baker's yeast; In water; at 20 ℃; for 144h; optical yield given as %ee; Enzymatic reaction;

DOI:10.1055/s-0028-1083364

Reference yield: 39.0%

bicyclo[3.3.1]nonane-2,6-dione (16473-11-3) → 6-hydroxybicyclo[3.3.1]nonan-2-one (1092543-24-2) + (S,S)-bicyclo[3.3.1]nonane-2,6-dione (36415-87-9)

Guidance literature:

With baker's yeast; D-glucose; In water; at 32 ℃; for 24h;

DOI:10.1016/j.tetasy.2008.05.009

upstream raw materials:

bicyclo[3.3.1]nonane-2,6-dione

(+)-(1S,2R,5S,6R)-bicyclo<3.3.1>nonane-2,6-diol

bicyclo[3.3.1]nonane-2,6-dione

C₂₉H₄₀O₈

Downstream raw materials:

(S,S)-6-methylbicyclo[3.3.1]nona-6-en-2-one 4-methylbenzenesulfonhydrazone

Refernces

• 1、 Malinauskiene, Julè,Kadziauskas, Petras,Malinauskas, Albertas,Kulys, Juozas. "Enzymatic enantioseparation of bicyclo[3.3.1]nonane-2,6-diones". . p. 1513 - 1517. Retrieved 1999.
• 2、 Carlquist, Magnus,Wallentin, Carl-Johan,Waernmark, Kenneth,Gorwa-Grauslund, Marie F.. "Genetically engineered Saccharomyces cerevisiae for kinetic resolution of racemic bicyclo[3.3.1]nonane-2,6-dione". . p. 2293 - 2295. Retrieved 2008.
• 3、 Egunlusi, Ayodeji O.,Malan, Sarel F.,Omoruyi, Sylvester I.,Ekpo, Okobi E.,Palchykov, Vitalii A.,Joubert, Jacques. "Open and rearranged norbornane derived polycyclic cage molecules as potential neuroprotective agents through attenuation of MPP+- and calcium overload-induced excitotoxicity in neuroblastoma SH-SY5Y cells". . . Retrieved 2020/07/27.
• 4、 Hiroi, Yuki,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi. "Asymmetric cross-dimerization between methyl methacrylate and substituted alkene by Ru(0)-bicyclononadiene complex". supporting information. p. 2486 - 2489. Retrieved 2013/07/05.