4-(Propan-2-ylidene)cyclohexan-1-one

Base Information

• Chemical Name: 4-(Propan-2-ylidene)cyclohexan-1-one
• CAS No.: 19620-36-1
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• DSSTox Substance ID: DTXSID10507030
• Nikkaji Number: J721.305K
• Wikidata: Q82363041
• Mol file: 19620-36-1.mol

Synonyms:4-(Propan-2-ylidene)cyclohexan-1-one;19620-36-1;4-isopropylidene cyclohexanone;SCHEMBL7495765;DTXSID10507030;UJYNKPIXFNHCOE-UHFFFAOYSA-N;4-(1-methylethyliden) cyclohexanone

Chemical Property of 4-(Propan-2-ylidene)cyclohexan-1-one

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 161

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C1CCC(=O)CC1)C

Technology Process of 4-(Propan-2-ylidene)cyclohexan-1-one

There total 12 articles about 4-(Propan-2-ylidene)cyclohexan-1-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: 92.0%

8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane (19620-35-0) → 4-(propan-2-ylidene)cyclohexan-1-one (19620-36-1)

Guidance literature:

With water; toluene-4-sulfonic acid; In acetone; for 3.5h; Reflux;

Reference yield:

nopinone (24903-95-5) + sulfuric acid (7664-93-9) → 4-(propan-2-ylidene)cyclohexan-1-one (19620-36-1) + cryptone (2158-59-0,2158-61-4,100295-52-1,500-02-7)

Guidance literature:

dextrorotatory form;

Reference yield:

→ 4-(propan-2-ylidene)cyclohexan-1-one (19620-36-1)

Guidance literature:

With barium carbonate; at 285 - 320 ℃;

upstream raw materials:

nopinone

4-chloro-4-(1'-methylethyl)cyclohexan-1-one

N,N-dimethyl-aniline

8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane

Downstream raw materials:

γ-terpineol

4-(α-bromo-isopropyl)-cyclohexanone

1,4-Cyclohexanedione

4-isopropylidene-cyclohexanone-(2,4-dinitro-phenylhydrazone)

Refernces

The Interaction of π orbitals with a carbocation over three σ bonds

10.1021/jo951643d

The study investigates the semi-π analogue of double hyperconjugation, known as "hyperconjugation/conjugation," in 4-isopropylidenecyclohexyl mesylate (4-OMs) and compares it with the saturated analogue, trans-4-isopropylcyclohexyl mesylate (5-OMs). The researchers found that the unsaturated substrate 4-OMs reacts only four times faster than the saturated substrate 5-OMs in 97% trifluoroethanol, indicating no significant through-bond interaction of the double bond with the reactive center. This is attributed to less than ideal overlap of the γ,δ π orbitals with the R, σ orbitals. However, when an electron-rich tin atom is attached to the 4-position, it provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation. The study concludes that the π bond does not effectively stabilize positive charge through two stages of conjugation in the studied system, suggesting that the hyperconjugation/conjugation mode may not be a viable mechanism under the given conditions.