Ethenylidenecyclopropane

Base Information

• Chemical Name: Ethenylidenecyclopropane
• CAS No.: 27567-84-6
• Molecular Formula: C5H6
• Molecular Weight: 66.1026
• DSSTox Substance ID: DTXSID60511940
• Nikkaji Number: J1.561.307F
• Wikidata: Q82370980
• Mol file: 27567-84-6.mol

Synonyms:ethenylidenecyclopropane;vinylidenecyclopropane;27567-84-6;Vinylidene-cyclopropane;DTXSID60511940

Chemical Property of Ethenylidenecyclopropane

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 66.0469501914
• Heavy Atom Count: 5
• Complexity: 78.2

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=C1CC1

Technology Process of Ethenylidenecyclopropane

There total 1 articles about Ethenylidenecyclopropane 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:

N-nitroso-N-spiropentyl urea (199783-43-2) → ethenylidenecyclopropane (27567-84-6) + cyclopropane (75-19-4) + spiropentane (157-40-4)

Guidance literature:

With potassium carbonate; 4-methoxy-phenol; In dichloromethane; at 5 - 7 ℃;

DOI:10.1007/s11172-008-0225-2

Reference yield: 52.0%

diazoacetic acid ethyl ester (623-73-4) + ethenylidenecyclopropane (27567-84-6) → 2-cyclopropylidene-cyclopropanecarboxylic acid ethyl ester (136028-47-2)

Guidance literature:

With dirhodium tetraacetate; In diethyl ether;

DOI:10.1021/jo00021a041

Reference yield:

ethenylidenecyclopropane (27567-84-6) + dimethyl sulfate (77-78-1) → methylcyclopropylacetylene (35201-01-5) + ethylidene-cyclopropane (18631-83-9)

Guidance literature:

ethenylidenecyclopropane; With lithium; In tetrahydrofuran; diethyl ether; at -40 ℃;

dimethyl sulfate; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0022-328X(01)01195-0

upstream raw materials:

N-nitroso-N-spiropentyl urea

Downstream raw materials:

2-cyclopropylidene-cyclopropanecarboxylic acid ethyl ester

bicyclopropylidene

dispiro[2.0.2⁴.1³]heptane

1-iodo-2-(2-ethoxypropyl)-1-cyclobutene

Refernces

Reactions of vinylidenecyclopropanes with xanthydrol and xanthene

10.1016/j.tet.2010.07.004

The research discusses the reactions of vinylidenecyclopropanes (VDCPs) with xanthydrol and xanthene, exploring their ring-opening reactions under specific conditions to yield conjugate triene derivatives. The study aimed to investigate the effects of different substituents on the reaction outcomes and to propose plausible reaction mechanisms based on previous literature and control experiments. The researchers used BF3·OEt2 as a catalyst with xanthydrol and DDQ with xanthene, conducting the reactions in 1,2-dichloroethane (DCE) at 0°C. The reactions resulted in moderate to good yields of conjugate triene derivatives, which were further transformed into novel spiro-alkanes using BF3·OEt2 at 70°C. The study concluded that these reactions provided a versatile method for synthesizing complex molecular structures and shed light on the reaction mechanisms involved, with further work underway to elucidate the mechanistic details and determine the scope and limitations of the reaction.