Cyclohexanone, 3-(tributylstannyl)-

Base Information

• Chemical Name: Cyclohexanone, 3-(tributylstannyl)-
• CAS No.: 63831-51-6
• Molecular Formula: C₁₈H₃₆OSn
• Molecular Weight: 387.193
• DSSTox Substance ID: DTXSID20404501
• Mol file: 63831-51-6.mol

Synonyms:Cyclohexanone, 3-(tributylstannyl)-;63831-51-6;3-TRIBUTYLSTANNANYL-CYCLOHEXANONE;DTXSID20404501;AKOS024427296

Chemical Property of Cyclohexanone, 3-(tributylstannyl)-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 388.178818
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C1CCCC(=O)C1

Technology Process of Cyclohexanone, 3-(tributylstannyl)-

There total 8 articles about Cyclohexanone, 3-(tributylstannyl)- 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: 88.0%

cyclohexenone (930-68-7) + tri-n-butyltin lithium (4226-01-1) → 3-(tri-n-butyl)stannylcyclohexan-1-one (63831-51-6,149655-22-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h;

Reference yield: 88.0%

cyclohexenone (930-68-7) + tributyltin chloride (1461-22-9) → 3-(tri-n-butyl)stannylcyclohexan-1-one (63831-51-6,149655-22-1)

Guidance literature:

tributyltin chloride; With naphthalene; lithium; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

cyclohexenone; In tetrahydrofuran; at -78 ℃; for 0.05h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.5b06587

Reference yield: 86.0%

n-butyllithium (109-72-8,29786-93-4) + (+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine (72170-87-7) + bis(tri-n-butyltin) (813-19-4) → (S)-3-tributylstannylcyclohexanone (63831-51-6,149655-22-1)

Guidance literature:

With NH₄Cl; O₃; In tetrahydrofuran; addn. of distannane to n-BuLi, cooling after 2 h to -100°C, warming to -78°C, dropwise addn. of the pyrrolidine compd., addn. of NH4Cl, evapn., dissolving in Et2O, washing (H2O, satd. NaCl), concn. and ozonolysis (CH2Cl2, -78°C); removing of the O3 with Ar, warming, evapn. and column chromy. (silica gel, petroleum ether-Et2O); ee 42 %;

upstream raw materials:

cyclohexenone

trimethylsilyltributyltin

tributyltin chloride

tri-n-butyltin lithium

Downstream raw materials:

5-hexenoic acid

(1R,3R)-3-Tributylstannanyl-cyclohexanol

(1S,3R)-3-Tributylstannanyl-cyclohexanol

1-phenyl-3-(tributylstannyl)cyclohexanol