68236-05-5

Basic information

• Product Name: 4,7-Tridecadienoic acid, ethyl ester, (Z,E)-
• CAS NO: 68236-05-5
• Molecular Formula: C15H26O2
• Molecular Weight: 238.37
• Mol File: 68236-05-5.mol

Chemical Properties

• CAS DataBase Reference: 4,7-Tridecadienoic acid, ethyl ester, (Z,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-Tridecadienoic acid, ethyl ester, (Z,E)-(68236-05-5)
• EPA Substance Registry System: 4,7-Tridecadienoic acid, ethyl ester, (Z,E)-(68236-05-5)

Safety Data

• Hazardous Substances Data: 68236-05-5(Hazardous Substances Data)

Upstream product

• 18495-27-7 1-bromooct-2-yne 
• 20739-58-6 2-octyn-1-ol 
• 112182-98-6 2-(1-Vinyl-non-3-ynyloxy)-tetrahydro-pyran 
• 112183-00-3 2-((Z)-1-Vinyl-non-3-enyloxy)-tetrahydro-pyran 
• 56722-26-0 1-bromo-(2E,5Z)-2,5-undecadiene 
• 101020-36-4 (Z)-undec-5-en-2-yn-1-ol 
• 56722-24-8 (2E,5Z)-2,5-undecadien-1-ol 
• 1573-66-6 hex-1-en-5-yn-3-ol 
• 72538-17-1 undec-1-en-5-yn-3-ol 
• 110-53-2 1-Bromopentane 
• 111-25-1 1-bromo-hexane 
• 101020-37-5 ethyl 2-carbethoxy-(4E,7Z)-4,7-tridecadienoate 
• 111285-93-9 ethyl (4E)-tridecen-7-ynoate 
• 56722-23-7 (5Z)-1,5-undecadien-3-ol 

Downstream Products

• 57981-60-9 (4E,7Z)-4,7-tridecadien-1-yl acetate 
• 57981-61-0 (4E,7Z)-4,7-Tridecadien-1-ol 

Relevant articles and documents

Insect pheromones and their analogs LV. Synthesis of trideca-4E,7Z-dien-1-yl acetate - Component of the sex pheromone of Phthorimaea opercucella

Starting from propargyl alcohol and using the thermal Claisen rearrangement at the stage of constructing the (E)-double bond, we have synthesized trideca-4E, 7Z-dien-1-yl acetate - a component of the sex pheromone of the potato moth Phthorimaea opercucella (Zeller).

Synthesis of 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella sex pheromone

A new synthetic approach to 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella (Zeller) potato moth sex pheromone, was developed using a highly stereoselective Claisen rearrangement and Wittig reaction.

Synthesis of Pheromones of Potato Tuberworm Moth, Phthorimaea opericulella (Zeller)

The alcohol (3) having highly flexible dual functionality (terminal acetylene and a terminal double bond), has been utilised for the synthesis of (n,n+3) alkadienes.The simplicity of this procedure has been illustrated by the synthesis of potato tuberworm moth pheromones, PTM-1 (1a) and PTM-2 (1b).

Synthesis of (4E,7Z)-4,7-Tridecadienyl Acetate and (4E,7Z,10Z)-4,7,10-Tridecatrienyl Acetate - The Sex Pheromones of Potato Tuberworm Moth

(4E,7Z)-4,7-Tridecadienyl acetate (1) and (4E,7Z,10Z)-4,7,10-tridecatrienyl acetate (2), the sex pheromones of potato tuberworm moth have been synthesized from a common intermediate 1-hexen-5-yn-3-ol (3) employing Claisen rearrangement as a key step to generate the trans-double bond.

Synthesis of (4E,7Z)-4,7-tridecadien-1-yl Acetate

(Z)-5-Undecen-2-yn-1-ol (II) on reduction with LAH produces (2E,5Z)-2,5-undecadien-1-ol (III) which gives the bromide (IV) on treatment with PBr3/ pyridine.The diester (V) resulting from alkylation of diethylmalonate with IV on decarbethoxylation generates ethyl (4E,7Z)-4,7-tridecadienoate (VI) which on reduction with lithium aluminium monoethoxy hydride affords (4E,7Z)-4,7-tridecadien-1-ol (VII).The dienol (VII) converts into the title compound (I) on reaction with acetic anhydride/ pyridine.