65733-18-8

Basic information

• Product Name: S-HYDROPRENE
• Synonyms: s-hydroprene (bsi,ansi,esa,e-iso);FYQGBXGJFWXIPP-OJROSNHMSA-N
• CAS NO: 65733-18-8
• Molecular Formula: C17H30O2
• Molecular Weight: 266.422
• Mol File: 65733-18-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: bp0.05 80°
• Flash Point: >100 °C
• Appearance: /
• Density: 0.886 g/cm³
• Vapor Pressure: 9.36E-05mmHg at 25°C
• Refractive Index: 1.461
• BRN: 5255711
• CAS DataBase Reference: S-HYDROPRENE(CAS DataBase Reference)
• NIST Chemistry Reference: S-HYDROPRENE(65733-18-8)
• EPA Substance Registry System: S-HYDROPRENE(65733-18-8)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3082 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 65733-18-8(Hazardous Substances Data)

Usage

Uses

Insect growth regulator; insecticide.

InChI:InChI=1/C17H30O2/c1-6-19-17(18)13-16(5)12-8-11-15(4)10-7-9-14(2)3/h8,12-15H,6-7,9-11H2,1-5H3/b12-8+,16-13+/t15-/m0/s1

Upstream product

• 60018-13-5 3,7-dimethyl-1-octanal 
• 58223-29-3 ethyl (2E,4E)-3,7,11-trimethyl-2,4,10-dodecatrienoate 
• 65733-16-6 (S)-methoprene 
• 1609-47-8 diethyl dicarbonate 
• 107-82-4 i-pentyl bromide 
• 86414-36-0 (S)-(-)-2,6,10-dimethylnonanal 
• 909879-22-7 methyl (R)-5-bromo-4-methylpentanoate 
• 87187-92-6 4(S),8-dimethylnonan-1-ol 
• 141-97-9 ethyl acetoacetate 
• 1356399-81-9 C₁₁H₂₃BO₂ 
• 122135-84-6 ethyl (E)-3-(trifluoromethylsulfonyloxy)but-2-enoate 
• 1007833-75-1 C₁₁H₂₀ 
• 1356399-80-8 C₁₁H₂₂Br₂ 
• 329327-50-6 ethyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate 

Relevant articles and documents

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.

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.

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.