Trogoderma granarium sex pheromone and preparation method thereof
The technology for the beetle and pheromone is applied in the field of the beetle sex pheromone and its preparation, which can solve the problems of difficult separation, low yield of the beetle sex pheromone and high cost, and achieves easy separation, High yield, yield-enhancing effect
Inactive Publication Date: 2019-01-25
NORTHWEST A & F UNIV
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Problems solved by technology
[0005] In view of this, the embodiment of the present invention provides a sex pheromone and its preparation method, the main purpose of which is to solve the problems of low yield, difficult separation and high cost of the sex pheromone in the synthesis process
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Embodiment 1
[0057] Preparation of Compound A: Triphenylphosphine (15.32g, 58.40mmol) and 5-mercapto-1phenyltetrazolium (10.41g, 58.40mmol) were placed in a 250mL three-necked flask under electromagnetic stirring under the protection of argon, and (R )-2-Methylbutanol (5.30mL, 4g, 48.67mmol) in anhydrous tetrahydrofuran solution was added to a three-necked flask, the system was placed in an ice bath, slowly drip diisopropyl azodicarboxylate (DIAD) (11.58) mL, 11.81g, 58.40mmol), stirred for 8h, detected by TLC. The solvent was spin-dried, and the column was eluted with a PE:EA gradient to obtain 10.53g of compound A (colorless and transparent liquid) with a yield of 87.3%; [α] 21 D =+11.52 (c=0.1, CHCl3); the structure of compound A was verified by NMR spectrum.
[0058] Preparation of compound B: Take compound A (1.14g, 4.59mmol) in a 100mL flask, add 20mL of dichloromethane, add m-chloroperoxybenzoic acid (m-CPBA) (2.38g, 13.77mmol) under stirring, and react for 4h , TLC detects that the r...
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Abstract
The invention discloses trogoderma granarium sex pheromone and a preparation method thereof. The preparation method comprises the following steps: enabling (R)-2-methylbutanol to react with 5-sulfydryl-1-phenyltetrazole Mitsnobu to obtain A; enabling A to react with peroxy acid to obtain B; enabling 1,3-propanediol to react with benzyl chloride under an alkaline condition to obtain C; oxidizing Cto obtain a compound D; enabling B to react with D and hexamethyldisilamine lithium salt to obtain E; catalytically hydrogenating E by virtue of palladium to obtain F; enabling F, iodine, tertiary phosphine and imidazole to obtain G; obtaining H by using 1,8-octylene glycol and benzyl chloride and alkali; oxidizing H to obtain I; obtaining J by using I, carbon tetrabromide and triphenylphosphine Corey-Fush; obtaining K by using J and strong alkali; obtaining L by using K and G and alkali; obtaining M by using L, ethyl mercaptan and boron trifluoride diethyl etherate solution; catalytically hydrogenating M by virtue of metal to obtain N; and oxidizing N to obtain a target product, wherein a chemical name of the target product is (R,Z)-14-methylhexadeca-8-ene-1-aldehyde, thus obtaining the trogoderma granarium sex pheromone. The preparation method disclosed by the invention is low in cost and high in yield.
Description
Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a bark beetle sex pheromone and a preparation method thereof. Background technique [0002] Insect pheromones are trace chemicals used by insects to transmit information. They can cause other individuals of the same species to produce strong behavioral responses. Insect pheromones include sex pheromone, aggregation pheromone, warning pheromone and oviposition pheromone, among which sex pheromone is the most in-depth research and the most widely used. In nature, sex pheromones are generally released by female adults after sexual maturity, which stimulates chemoreceptors in the antennae of males of the same species, causing the males to impulse and fly towards the release source, and finally mate with females to reproduce offspring . The use of synthetic pheromone compounds can interfere with the information communication system of the pests, so it can effectively monitor th...
Claims
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IPC IPC(8): C07C45/30C07C47/21
CPCC07C17/16C07C29/00C07C29/17C07C29/172C07C41/16C07C41/24C07C41/30C07C45/30C07D257/04C07C43/1782C07C47/277C07C43/164C07C31/125C07C19/07C07C43/172C07C43/15C07C33/042C07C33/025C07C47/21
Inventor 张涛杜振亭
Owner NORTHWEST A & F UNIV