VINYLCYCLOPROPANE

Base Information

• Chemical Name: VINYLCYCLOPROPANE
• CAS No.: 693-86-7
• Molecular Formula: C5H8
• Molecular Weight: 68.1185
• Hs Code.: 2902199090
• Mol file: 693-86-7.mol

Synonyms:Cyclopropane,ethenyl-;cyclopropyl-;

Chemical Property of VINYLCYCLOPROPANE

Chemical Property:

• Vapor Pressure: 589mmHg at 25°C
• Melting Point: -109.81 °C
• Refractive Index: 1.578
• Boiling Point: 32.114 °C at 760 mmHg
• PSA: 0.00000
• Density: 0.919 g/cm³
• LogP: 1.58240
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Sparingly)

Purity/Quality:

99% ^*data from raw suppliers

Vinylcyclopropane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Vinylcyclopropane is a useful synthetic intermediate. Vinylcyclopropane and its derivatives can participate in a variety of transition-metal-catalyzed multicomponent cycloadditions to produce five- to eight-membered carbocycles.

Technology Process of VINYLCYCLOPROPANE

There total 7 articles about VINYLCYCLOPROPANE 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: 5.0%

1,4-Pentadiene (591-93-5) → 1-methylbuta-1,3-diene (2004-70-8,17410-45-6,25212-15-1,64940-84-7) + ethenylcyclopropane (693-86-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + cyclopentene (142-29-0)

Guidance literature:

Product distribution; Mechanism; Plasmolysis (40 W, 3.48mmol/min, 13.56 MHz);

DOI:10.1016/S0040-4039(00)85657-9

Reference yield:

cyclopentene (142-29-0) → cyclopent-1->3-enyl (10577-65-8) + bicyclo[2.1.0]pentane (185-94-4) + ethenylcyclopropane (693-86-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8)

Guidance literature:

at 526.9 ℃; Rate constant; pyrolysis, other temperature;

DOI:10.1021/j100238a019

Reference yield:

1,4-Pentadiene (591-93-5) → ethenylcyclopropane (693-86-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + cyclopentene (142-29-0)

Guidance literature:

Title compound not separated from byproducts; Irradiation;

DOI:10.1021/jo00203a006

upstream raw materials:

2-ethoxy-ethanol

(±)-(1-chloroethyl)cyclopropane

1,4-Pentadiene

cyclopentene

Downstream raw materials:

1-cyclopropylethane-1,2-diol

cyclopropanecarboxylic acid

(2-cyclopropylethene-1,1-diyl)dibenzene

1-cyclopropylethanol

Refernces

Rh(i)-catalyzed intramolecular [3 + 2] cycloaddition reactions of 1-ene-, 1-yne- and 1-allene-vinylcyclopropanes

10.1039/b922417c

The study explores the development of new reactions for constructing five-membered carbocycles, particularly those embedded in polycyclic structures, which are ubiquitous in organic molecules. The authors designed a new type of substrate, 1-ene/yne-VCP, by tethering the two-carbon component to the C(1)-position of vinylcyclopropane (VCP) to achieve a rhodacyclohexene intermediate with a new substitution pattern. The optimized reaction conditions using [Rh(dppp)]SbF6 as the catalyst resulted in high selectivity and yield for the [3 + 2] cycloadducts. Various 1-ene/yne-VCP substrates were tested, yielding moderate to excellent results and demonstrating the versatility of the method. The study also explored the stereoinduction in the [3 + 2] cycloaddition process and extended the reaction to 1-allene-substituted VCP. Control experiments confirmed the crucial role of the vinyl group in the transformation. The proposed mechanism involves the formation of a p-allyl rhodacyclohexene intermediate, followed by insertion and reductive elimination steps.