5-Hepten-2-ol, 6-methyl

CAS 515-69-5 EINECS/ELINCS 208-205-9 Synonyms a-4-Dlmethyl-a-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol 5-Hepten-2-ol, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl) 6-Methyl-2-(4-methyl-3-cyclohexen-1 -yl)-5-hepten-2-ol Classification Terpene Empirical C16H26O Properties M.w. 222.41... 

Hepten-2-ol, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl). SeeBisabolol 5-Hepten-2-one, 6-methyl-. See Methyl heptenone Heptenophos... 

Methyl-5-hepten-2-ol CAS 1569-60-4 EINECS/ELINCS 216-377-1 Synonyms 5-Hepten-2-ol, 6-methyl-Empirical CsHieO... 

Methyl-5-heptene-2-one Methyl-5-hepten-2-ol. See Methyl heptenone... 

Synonyms 5-Hepten-2-one, 6-methyl- 6-Methyl-5-heptene-2-one Methyl-5-hepten-2-ol 2-Methyl-2-hepten-6-one 6-Methyl-5-hepten-2-one... 

Wang, K. Ying, X.-G. Xia, M.-S. Xia, J.-Z. Hu, Y. Isobarie vapor-liquid equilibria for 6-methyl-5-hepten-2-one + bis(3-methyl-2-butenyl) ether, bis(3-methyl-2-butenyl) ether -1- 3,3-dimethyl-2-propen-l-ol, 3,3-dimethyl-2-propen-l-ol + 6-methyl-5-hepten-2-one, and 6-methyl-5-hepten-2-one + 6-methyl-3-isopropenyl-5-hepten-2-one binary systems. J. Chem. Eng. Data 1989, 34, 126-130. 

Figure 13.10 DEPT-NMR spectra for 6-methyl-5-hepten-2-ol. Part fa) is an ordinary broadband-decoupled spectrum, which shows signals for all eight carbons. Part [b) is a DEPT-90 spectrum, which shows only signals for the two CH carbons. Part (c) is a DEPT-135 spectrum, which shows positive signals for the two CH and three CH3 carbons and negative signals for the two CH2 carbons.

Problem 13.9 Assign a chemical shift to each carbon in 6-methyl-5-hepten-2-ol (Figure 13.10). Problem 13.10 Estimate the chemical shift of each carbon in the following molecule. Predict which... 

DEPT-NMR spectrum. 6-methyl-5-hepten-2-ol, 451 Detergent, structure of, 1065 Deuterium isotope effect, 386-387 El reaction and, 392 E2 reaction and, 386-387 Dewar benzene. 1201 Dextromethorphan, structure of, 294 Dextrorotatory, 295 Dextrose, structure of. 973 Dialkylamine, pKa of, 852 Diastereomers, 302-303 kinds of, 310-311 Diastereotopic (NMR), 456... 

N-Methylcyclohexylamine, 13C NMR spectrum of, 954 1H NMR spectrum of, 953 Methylene group, 178 N-Methylguanine, electrostatic potential map of, 1121 6-Methyl-5-hepten-2-ol, DRPT-NMR spectra of. 451... 

By synthesizing pure enantiomers of pheromones, various stereochemistry-pheromone activity relationships could be clarified. For example, in the case of sulcatol (6-methyl-5-hepten-2-ol),both the enantiomers are necessary for bioactivity. For other relationships, please refer to [4-9]. 

The first suitable representative of this class of substances, 6-methyl-5-heptene-2-one, was investigated by Neuberg and Lewite. This ketone, which is a natural constituent of ethereal oils, can also be obtained by degradation of various aliphatic and cyclic terpenes. By means of fermenting yeast it is converted to 6-methyl-5-heptene-2-ol,... 

Additional examples are the synthesis of the pheromone (iS )-6-methyl-5-hepten-2-ol (S-sulca-tol) (8)61 and of (/t)-2,3-epoxypropyl butanolate (9)62, which serves as the starting material in the synthesis of the -blocker l-(l-naphthenyloxy)-3-isopropylamino-2-propanol10. 

Bisabolene-type sesquiterpenes, e.g. a-bisabolene 74 (Structure 4.20), are widely distributed in nature. This sesquiterpene hydrocarbon is a constituent of bergamot, myrrh and a wide variety of essential oils. Its oxygenated derivatives a-bisabolol [6-methyl-2-(4-methyl-3-cyclohexen-l-yl)-5-hepten-2-ol] 75 and -bisabolol [4-methyl-l-(6-methylhept-5-en-2-yl)cyclohex-3-enol] 76 are found abundantly in chamomile. 

The situation is summarized from a slightly different perspective in Figure 2.2. Here, data obtained using the same set of organic solvents have been plotted. The porcine pancreatic lipase-catalyzed transesterification of sulcatol (6-methyl-5-hepten-2-ol) with butyric acid trifluoroethyl ester [81] has been chosen (arbitrarily) to calibrate the solvents. It is clear that, irrespective of the solvent descriptors that one may aim to investigate, different systems are seen to respond differently to the same (change of) medium. 

Comparable results were also reported by another group [65]. Controlled conversion of 6-methyl-5-hepten-2-one by Botrytis cinerea resulted in the formation of (5)-(+)-6-methyl-5-hepten-2-ol (sulcatol) of 90% ee. In addition, (2R,5R), (25,55)-, (2R,5S) and (25,5/ )-pityol and the four enantiomers of 3-hydroxy-2,2,6-trimethyltetrahydropyran were found as biotransformation products of 6-methyl-5-hepten-2-one. 

Mori K. and Puapoomchareon P. (1987) Conversion of the enantiomers of sulcatol (6-methyl-5-hepten-2-ol) to the enantiomers of pityol [fra s-2-(l-hydroxy-1-methylethyl)-5-methyltetrahydrofuran], a male-specific attractant of the bark beetle Pityophthorus pityographus. Liebigs Annalen der Chemie 3, 271-272. 

In the same way, 6-methyl-5-hepten-2-one (entry 2) can conveniently be converted into 6-methyl-5-hepten-2-ol (sulcatol), which in its (R) configuration is an insect pheromone. 

A population aggregation pheromone has been identified from males of the scolytid, Gnathotrichus sulcatus (69). A 65/35 mixture of the (S)-(+) and the (R)-(-) enantiomers of 6-methyl-5-hepten-2-ol (sulcatol) was isolated from the boring dust and shown to attract both females and males in a ratio of 2.65 1, respectively. 

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