17904-27-7

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 4-(1,5-dimethyl-3-oxohexyl)-, methyl ester, (1R,4R)-(+)-
• Synonyms: 1-Cyclohexene-1-carboxylic acid, 4-(1,5-dimethyl-3-oxohexyl)-, methyl ester, (1R,4R)-(+)-;(4R)-4-[(1R)-1,5-Dimethyl-3-oxohexyl]-1-cyclohexene-1-carboxylic acid methyl ester;(4R)-4α-[(1R)-1,5-Dimethyl-3-oxohexyl]-1-cyclohexene-1-carboxylic acid methyl ester;(R)-4-[(R)-1,5-Dimethyl-3-oxohexyl]-1-cyclohexene-1-carboxylic acid methyl ester;threo-Juvabione
• CAS NO: 17904-27-7
• Molecular Formula: C₁₆H₂₆O₃
• Molecular Weight: 266.38
• Mol File: 17904-27-7.mol

Chemical Properties

• Boiling Point: 351.9°Cat760mmHg
• Flash Point: 150.4°C
• Appearance: /
• Density: 0.995g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 4-(1,5-dimethyl-3-oxohexyl)-, methyl ester, (1R,4R)-(+)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 4-(1,5-dimethyl-3-oxohexyl)-, methyl ester, (1R,4R)-(+)-(17904-27-7)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 4-(1,5-dimethyl-3-oxohexyl)-, methyl ester, (1R,4R)-(+)-(17904-27-7)

Safety Data

• Hazardous Substances Data: 17904-27-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H26O3/c1-11(2)9-15(17)10-12(3)13-5-7-14(8-6-13)16(18)19-4/h7,11-13H,5-6,8-10H2,1-4H3/t12-,13+/m1/s1

Upstream product

• 926-62-5 isobutylmagnesium bromide 
• 73484-31-8 (S)-4-((S)-2-Chlorocarbonyl-1-methyl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 295356-97-7 (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol 
• 295357-00-5 [3-methyl-1-(methylthio)butyl]diphenylphosphine oxide 
• 295356-98-8 (+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester 
• 295356-99-9 (+)-(4R)-[(S)-methyl-2-oxoethyl]cyclohex-1-enecarboxylic acid methyl ester 
• 145353-87-3 (3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one 
• 46941-66-6 (3-methylbutan-1-yl)(diphenyl)phosphine oxide 
• 935476-09-8 (6R)-2-methyl-6-((1S,4S)-4-triethylsiloxycyclohex-2-enyl)heptan-4-ol 
• 935476-06-5 (3R)-((1S,4S)-4-triethylsiloxycyclohex-2-enyl)butyraldehyde 
• 935476-05-4 (1R,4R,5R,8S)-8-triethylsiloxy-4-methylbicyclo[3.3.1]nonan-2-one 
• 935476-04-3 (1R,4R,5R,8S)-8-hydroxy-4-methylbicyclo[3.3.1]nonan-2-one 
• 935476-03-2 (1R,4R,5R,8S)-8-methoxymethoxy-4-methylbicyclo[3.3.1]nonan-2-one 
• 935476-11-2 C₁₅H₂₆O₂ 

Downstream Products

• 6753-22-6 (+/-)-Epitodomatusaeure 
• 57495-79-1 4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid methyl ester 
• 38963-91-6 4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid 
• 38963-91-6 4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid 
• 86279-09-6 cis-4-<3(S)-hydroxy-1(R),5-dimethylhexyl>cyclohexane-1-carboxylic acid 
• 86279-09-6 trans-4-<3(S)-hydroxy-1(R),5-dimethylhexyl>cyclohexane-1-carboxylic acid 
• 17844-06-3 (R)-4-((R)-3-Hydroxy-1,5-dimethyl-hexyl)-cyclohex-1-enecarboxylic acid 
• 38963-60-9 4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid methyl ester 
• 58493-52-0 methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate 
• 132185-48-9 (+)-oxoepijuvabione 
• 6753-22-6 todomatuic acid 

Relevant articles and documents

Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation

(+)-Juvabione, a natural sesquiterpene exhibiting insect juvenile hormone activity, has been synthesized from σ-symmetric 4-(2-formylethyl) cyclohexanone by employing organocatalytic asymmetric aldolisation and Norrish I-type fragmentation as the key step

Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione

The novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement shows a high diastereoselectivity for the Ireland-Claisen rearrangement starting from the endo-product of the Diels-Alder reaction. Based on this mechanistic knowledge, the novel tandem process could be applied to the synthesis of rac-juvabione.

A lipase-mediated route to (+)-juvabione and (+)-epijuvabione from racemic norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized from (±)-norcamphor via the both enantiomeric intermediates having bicyclo[3.2.1]octane framework by employing a lipase-mediated kinetic ester-hydrolysis reaction and cyclopropane ring-expansion reaction as the key steps.

Stereo- and Enantio-controlled Synthesis of (+)-Juvabione and (+)-Epijuvabione from (+)-Norcamphor

(+)-Juvabione and (+)-epijuvabione, natural sesquiterpenes exhibiting insect juvenile hormone activity, have been synthesized with complete stereo- and enantio-control using (+)-norcamphor as the chiral precursor via both the enantiomeric bicyclooc

Synthesis of compounds with juvenile hormone activity; XXXI: Stereocontrolled synthesis of (+)-juvabione from a chiral sulfoxide

A stereocontrolled synthesis of (+)-juvabione is described. The key step is a regioselective lithiation of a chiral (E)-butenyl sulfoxide 5 followed by stereoselective 1,4-addition to cyclohex-2-en-1-one. The chiral sulfoxide 5 was prepared by employing a

Synthesis of (+)-Juvabione, a Compound with Juvenile Hormone Activity

(+)-Juvabione 1 was synthesized by employing (1R,4S,6S)-6-hydroxybicyclooctan-2-one 2 as a chiral source. (+)-Juvabione 1 shows juvenile hormone activity, and its racemate has been repeatedly synthesized.Optically active 1 was synthesized by Pawson

EFFICIENT STEREOSELECTIVE SYNTHESIS OF BOTH (+/-)-JUVABIONE AND (+/-)-EPI-JUVABIONE BY NEW EXTRACYCLIC STEREOCONTROL METHODOLOGY

The Hosomi-Sakurai reactions of E- and Z-crotylsilanes with cyclohexenone at -78 degC showed respectively high erythro and relatively low threo selectivities, modification of the silyl substituents giving a variable effect.In the reaction with Z-alkoxycrotylsilanes, the threo selectivity could be improved by the utilization of the kinetic difference between the diastereomeric products 4 and 5 to the secondary cyclization.Starting from 4 and 5 thus obtained, the syntheses of both (+/-)-juvabione and (+/-)-epi-juvabione have been respectively achieved in a concise way.