65733-19-9

Upstream product

• 60018-13-5 3,7-dimethyl-1-octanal 
• 72962-76-6 3E 6,10-dimethyl-3-undecen-2-one 
• 36678-63-4 ethoxyethynylmagnesium bromide 
• 58223-29-3 ethyl (2E,4E)-3,7,11-trimethyl-2,4,10-dodecatrienoate 
• 5988-91-0 (S)-3,8-Dimethyloctanal 
• 106-21-8 tetrahydrogeraniol 
• 68680-98-8 S-(-)-dihydrocitronellol 
• 106-22-9 Citronellol 
• 329327-50-6 ethyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate 
• 65733-16-6 (S)-methoprene 
• 1356399-80-8 C₁₁H₂₂Br₂ 
• 1007833-75-1 C₁₁H₂₀ 
• 1356399-81-9 C₁₁H₂₃BO₂ 
• 122135-84-6 ethyl (E)-3-(trifluoromethylsulfonyloxy)but-2-enoate 

Relevant academic research and scientific papers

Terpenes in organic synthesis 14. Synthesis of S-(+)-hydroprene from (+)-β-citronellene

A seven-step synthesis of S-(+)-hydroprene (S-1) in ca. 20percent overall yield starting from S-(+)-3,7-dimethyl-1,6-octadiene (2) of 55 +/- 10percent optical purity is described.The introduction of an optical enhancement step in the synthetic sequence at the stage of S-(-)-3,7-dimethyl-1-octanol (9) raises the optical purity of S-1 from ca. 50percent to ca. 80percent.

A juvenile hormone analogs of the preparation method

The invention relates to the field of insecticides, and particularly relates to a preparation method of a juvenile hormone analogue (which comprises S-methoprene and S-hydroprene). The preparation method of the juvenile hormone analogues comprises the following steps of: A. adding (2E, 4E)-11-R-3,7,11-trimethyl-2,4-dodecadienoic acid (R is hydrogen or methoxyl) serving as raw material, an organic alkali catalyst and an organic solvent to a reaction vessel, and starting stirring; B. dropwise adding an organic solvent (the same as the organic solvent in the step A) solution of pyrocarbonate; C. after the addition is completed, reacting at 0-30 DEG C for 0-3 hours; D. adding water to stop reaction, and splitting phases of reaction liquid to obtain an organic phase; E. carrying out reduced pressure concentration and distillation to obtain a product, wherein the steps can also be carried out under the condition that the addition sequences of the pyrocarbonate and an organic strongly-alkaline catalyst are exchanged. The preparation method disclosed by the invention has the advantages of mild reaction condition, high product purity, high yield, environment-friendly and safe route and good industrial prospect.

Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki-Miyaura cross-coupling

A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key Csp2-Csp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved.

Combined Biochemical and Electrochemical Approach to Chiral C10-Components for Juvenoid Synthesis, and Preparation of (2E,4E,7S)Stereoisomers of Metoprene and Hydroprene

Enantioselective acylation of (RS)-3,7-dimethyl-7-methoxyoctan-1-ol and (RS)-3,7-dimethyl-octan-1-ol with vinyl acetate in the presence of lipase from yeast Candida cylindracea was performed to conversion of 40-50%, and subsequent hydrolysis of the products afforded (S)-(-)-enantiomers of these alcohols with ee of 98-100%. The oxydation of these products by bromine generated by electrolysis in a membraneless device in the system "aqueous NaBr (+NaHCO3)/CH2Cl2" in the presence of 4-substituted 2,2,6,6-tetramethyl-1-oxopiperidinium salts furnished the corresponding (S)-(-)-alkanals. The condensation of the latter with the esters of 3-alkoxycarbonyl-2-methylprop-2-enylphosphonic acids in a heterophase system solid KOH-benzene-tetraoctylammonium bromide yielded samples of metoprene and hydroprene of high configurational purity.

Synthesis of S-(+)-hydroprene

A novel path to S-(+)-hydroprene (1) starting from the technical grade S-(+)-dihydromyrcene (2, e.e. > 50percent) is proposed.The latter was selectively transformed into S-3,7-dimethyloctanal (5) in three steps including hydroalumination.The reactions of 5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl2/CuCl or by ozonolysis, afford S,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in ca. 23percent overall yield.