41031-88-3

Basic information

• Product Name: 2-(2-cis-Pentenyl)-2-cyclopenten-1-one
• Synonyms: 2-(2-cis-Pentenyl)-2-cyclopenten-1-one;2-(2-cis-Pentenyl)-2-cyclopentenone;2-[(Z)-2-Pentenyl]cyclopenten-1-one
• CAS NO: 41031-88-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• Mol File: 41031-88-3.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-cis-Pentenyl)-2-cyclopenten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-cis-Pentenyl)-2-cyclopenten-1-one(41031-88-3)
• EPA Substance Registry System: 2-(2-cis-Pentenyl)-2-cyclopenten-1-one(41031-88-3)

Safety Data

• Hazardous Substances Data: 41031-88-3(Hazardous Substances Data)

Upstream product

• 52056-49-2 (Z)-1-(prop-1-en-1-yl)spiro[2.4]heptan-4-one 
• 42537-02-0 2-<(Z)-2-pentenyl>cyclopentanone 
• 22592-15-0 1-chloropent-2-yne 
• 627-93-0 hexanedioic acid dimethyl ester 
• 81159-43-5 methanesulfonic acid pent-2-ynyl ester 
• 68480-23-9 methyl 2-oxo-1-(pent-2-yn-1-yl)cyclopentanecarboxylate 
• 52056-46-9 5-(1,4-Dioxa-spiro[4.4]non-6-yl)-pent-3-yn-2-ol 
• 61856-14-2 1-nitro-dec-7c-en-4-one 
• 61856-12-0 (Z)-nona-1,6-dien-3-one 
• 66972-01-8 nona-1,6c-dien-3-ol 
• 5009-31-4 (Z)-1-Bromohex-3-ene 
• 72049-83-3 (Z)-1-hydroxydec-7-en-4-one 
• 88629-20-3 allyl 1-(2-pentynyl)-2-oxocyclopentanecarboxylate 
• 6261-22-9 pent-2-yn-1-ol 

Downstream Products

• 1101843-02-0 methyl jasmonate 
• 221682-41-3 (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid 
• 1211-29-6 methyl jasmonate 
• 488-10-8 cis-jasmone 

Relevant articles and documents

Tandem Thermal Reactions for the Synthesis of Jasmonoids

A tandem reaction tactic for the preparation of a jasmonoid intermediate consists of pyrolysis of a spiroannulated cyclopentanone. The thermal decomposition actually involves a retro-Diels-Alder reaction and a homo-1,5-hydrogen shift with cleavage of the cyclopropane unit.

PROCESS FOR PREPARING PERFUMING INTERMEDIATE

The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I) by a cross metathesis reaction. Said compound of formula (I) is valuable new chemical intermediate for producing perfuming ingredients and is also part of the present invention.

Route Scouting towards a Methyl Jasmonate Precursor

For the synthesis of methyl jasmonate (1), via the strategic intermediates 3, 4, and 6a, we constructed a synthetic network via the diverse intermediates 7-10, 13, 14, 17, and 18. This allowed us to compare the efficiency of more than 20 novel routes. The most productive pathway with a total yield of 38% is represented by the sequence→5a→5m→13b→13a→6a→4 and proceeds via sequential bromination, basic elimination, decarbomethoxylation, isomerization, and finally Lindlar hydrogenation. The shortest selective way, 2a→[(E,E)-12b]→3→4, is a two-pot sequence using a modification of Naef's method, based on an aldol condensation between inexpensive cyclopentanone (2a) and crotonaldehyde, with in situ Corey-Chaykovsky cyclopropanation under phase transfer conditions. The key intermediate 3 was then simply pyrolyzed to afford 4 in 27% total yield. The alternative isomerization method via the six-step deviation→5a→5c→8c→13a→6a→4 was longer, although more efficient, with a total yield of 32%. Alternatively, a yield of 34% was obtained via the five-step sequence→5a→5c→2h→2i→4. Another favored six-step pathway,→5a→5c→2h→17a→14a→4 afforded the target compound in 35% total yield.