Dispiro[5,1,5,1]-tetradecane-7,14-dione

Base Information

• Chemical Name: Dispiro[5,1,5,1]-tetradecane-7,14-dione
• CAS No.: 950-21-0
• Molecular Formula: C14H20 O2
• Molecular Weight: 220.312
• Mol file: 950-21-0.mol

Synonyms:NSC 22088

Chemical Property of Dispiro[5,1,5,1]-tetradecane-7,14-dione

Chemical Property:

• Vapor Pressure: 2.73E-06mmHg at 25°C
• Melting Point: 165-167℃
• Boiling Point: 390°Cat760mmHg
• Flash Point: 146.2°C
• PSA: 34.14000
• Density: 1.11g/cm³
• LogP: 3.03920

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Dispiro[5,1,5,1]-tetradecane-7,14-dione

There total 12 articles about Dispiro[5,1,5,1]-tetradecane-7,14-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: 65.0%

cyclohexanylcarbonyl chloride (2719-27-9) → dispiro[5.1.5.1]tetradecane-7,14-dione (950-21-0)

Guidance literature:

With triethylamine; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja109494b

Reference yield: 24.0%

1,4-thioxodispiro[5.1.58.16]tetradecan-7-one (22502-48-3) → dispiro[5.1.5.1]tetradecane-7,14-dione (950-21-0) + C14H20O2S

Guidance literature:

With triphenyl phosphite; ozone; Yield given. Multistep reaction; 1.) -80 deg C, methylene chloride 2.) room temperature, 2 h;

Reference yield:

trimethyl 2-oxo-1,2,3,9a-tetrahydro-3,9a-ethenocarbazole-1-spirocyclohexane-4,10,11-tricarboxylate (86340-63-8) → dispiro[5.1.5.1]tetradecane-7,14-dione (950-21-0) + Carbazol-1,2,4-tricarbonsaeuretrimethylester (37914-15-1) + dimethyl 4,6-dioxo-5,6-dihydro-4H-pyrido<3,2,1-jk>carbazole-5-spirocyclohexane-1,3-dicarboxylate (86340-49-0)

Guidance literature:

at 190 - 210 ℃; for 0.25h; under 0.1 - 0.2 Torr;

upstream raw materials:

cyclohexanylcarbonyl chloride

pentamethyleneketene

n-butyllithium

chloro-trimethyl-silane

Downstream raw materials:

1,4-thioxodispiro[5.1.5⁸.1⁶]tetradecan-7-one

Dispiro<5.1.5.1>tetradecane-7,14-dithione

methyl 1-(cyclohexylcarbonyl)cyclohexanecarboxylate

1-(1-cyclohexenyl)-1-methoxycarbonylcyclohexane

Refernces

• 1、 Kuzmanich, Gregory,Spaenig, Fabian,Tsai, Chao-Kuan,Um, Joann M.,Hoekstra, Ryan M.,Houk,Guldi, Dirk M.,Garcia-Garibay, Miguel A.. "Oxyallyl Exposed: An Open-Shell Singlet with Picosecond Lifetimes in Solution but Persistent in Crystals of a Cyclobutanedione Precursor". supporting information; experimental part. p. 2342 - 2345. Retrieved 2011/05/04.
• 2、 Calaminus, W.,Voegtle, F.,Eidenschink, R.. "Thermotropic Liquid Crystals Containing the Dispirotetradecane Unit". . p. 1011 - 1014. Retrieved 2007/10/02.