56221-90-0

Upstream product

• 54897-65-3 (Z)-3-Tetradecen-1-ol acetate 
• 112-29-8 1-bromo dodecane 
• 68900-86-7 trans-3-tetradecen-1-ol 
• 75-36-5 acetyl chloride 
• 139489-32-0 1-cyclopropyl-undecan-1-ol 
• 75730-21-1 trans-3-tetradecenoic acid 
• 112-54-9 Dodecanal 
• 108-24-7 acetic anhydride 
• 127-08-2 potassium acetate 
• 139489-34-2 1-bromo-tetradec-(3E)-en 

Downstream Products

• 68900-86-7 trans-3-tetradecen-1-ol 

Relevant academic research and scientific papers

Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate

The invention discloses a method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method comprises the following steps: (1) preparing 3-tetradecyne alcohol-1; (2) preparing cis-3-tetradecenol-1; (3) preparing trans-3-tetradecenol-1; and (4) preparing the cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method is used for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate which are main components of gyplure of holcocerus insularis Staudinger; the raw materials for reaction are easily obtained; the cost is low; technical processes are short; reaction conditions are mild; the operation is simple, convenient and free from risk; the product is easily separated; the yield is high; and massive production can be carried out.

Short and stereoselective synthesis of (E)-3-alkenyl acetates, insect sex pheromone constituents of Lepidoptera; Gelechidae

(E)-3-alkenyl acetates, which are insect sex pheromone constituents, have been prepared from linear saturated aldehydes, by a short three steps process, via the (E)-3-alkenoic acids and the corresponding (E)-3-alkenols, in good overall yield (60-65%) and high stereochemical purity (>99%).

SYNTHESIS OF 3E-TETRADECENOL, 3E,9E-TETRADECADIENOL, AND THEIR ACETATES STARTING FROM ACETYLCYCLOPROPANE

Stereospecific synthesis of the linear E-olefins mentioned in the title was realized by a general scheme that was worked out earlier by the authors and which includes as key step homologization of the corresponding aliphatic pentakisnoraldehydes by means of trimethylsilyloxyvinylcyclopropane and ZnBr2-initiated rearrangement of the intermediate cyclopropylcarbinols under the influence of Me3SiBr.

Olefin Inversion. 3. Preparations and Reductions of vic-Halohydrin Trifluoroacetates

Treatment of alkenes with N-bromo- and N-chlorosuccinimide in trifluoroacetic acid resulted in stereospecific anti addition of the elements of trifluoroacetyl hypobromite and hypochlorite, respectively.Heating the vic-bromo- or -chlorohydrin trifluoroacetates with NaI in DMF produced olefins with inversion of geometry.Treatment of the adducts with Zn in DMF reduced them to olefins with retention of geometry.Reductive transformations involving the chlorohydrin trifluoroacetates were virtually stereospecific, whereas those involving the bromohydrin trifluoroacetates were >90percent stereoselective for NaI reductions and only 60-90percent stereoselective for reductions by Zn.