Spiro[5.5]undec-1-en-3-one

Base Information

• Chemical Name: Spiro[5.5]undec-1-en-3-one
• CAS No.: 30834-42-5
• Molecular Formula: C11H16 O
• Molecular Weight: 164.2441
• Mol file: 30834-42-5.mol

Synonyms:NSC 286670

Chemical Property of Spiro[5.5]undec-1-en-3-one

Chemical Property:

• Vapor Pressure: 0.00404mmHg at 25°C
• Boiling Point: 279.4°Cat760mmHg
• Flash Point: 133.9°C
• PSA: 17.07000
• Density: 1g/cm³
• LogP: 2.85600

Purity/Quality:

98%min ^*data from raw suppliers

Spiro[5.5]undec-1-en-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spiro[5.5]undec-1-en-3-one

There total 14 articles about Spiro[5.5]undec-1-en-3-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: 70.0%

1-Formyl-1-(3-oxobutyl)cyclohexane (30834-43-6) → spiro[5.5]undec-1-en-3-one (30834-42-5)

Guidance literature:

With hydrogenchloride; In water; for 1h; Heating;

DOI:10.1016/S0040-4020(01)82058-5

Reference yield: 56.0%

methyl vinyl ketone (78-94-4,25038-87-3) + cyclohexanecarbaldehyde (2043-61-0) → spiro[5.5]undec-1-en-3-one (30834-42-5)

Guidance literature:

With sulfuric acid; In benzene; 1.) room temp.to reflux, 1h, 2.) reflux, 3h;

DOI:10.1021/jo01314a048

Reference yield: 14.0%

1-Vinyl-spiro[3.5]nonan-1-ol (152568-20-2) → spiro[5.5]undec-1-en-3-one (30834-42-5) + spiro[5.5]undecan-3-one (1890-25-1) + [2,2']Bi[spiro[5.5]undecyl]-3,3'-dione

Guidance literature:

With copper diacetate; Mn(pic)3; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo00077a054

upstream raw materials:

1-Formyl-1-(3-oxobutyl)cyclohexane

methyl vinyl ketone

cyclohexanecarbaldehyde

1-Vinyl-spiro[3.5]nonan-1-ol

Downstream raw materials:

Dichloro-acetic acid 3-oxo-spiro[5.5]undec-4-en-2-yl ester

Benzoic acid 3-oxo-spiro[5.5]undec-4-en-2-yl ester

spiro[5.5]undecane-3-carboxylic acid

spiro[5.5]undecan-3-amine hydrochloride

Refernces

• 1、 Leverenz, Malte,Merten, Christian,Dreuw, Andreas,Bach, Thorsten. "Lewis Acid Catalyzed Enantioselective Photochemical Rearrangements on the Singlet Potential Energy Surface". supporting information. p. 20053 - 20057. Retrieved 2019/12/30.
• 2、 Wang, Jun,Ma, Chunlong,Fiorin, Giacomo,Carnevale, Vincenzo,Wang, Tuo,Hu, Fanghao,Lamb, Robert A.,Pinto, Lawrence H.,Hong, Mei,Klein, Michael L.,Degrado, William F.. "Molecular dynamics simulation directed rational design of inhibitors targeting drug-resistant mutants of influenza A virus M2". supporting information; experimental part. p. 12834 - 12841. Retrieved 2011/10/08.