6-Methylcyclohex-3-ene-1-carboxylic acid → HCID 11208673、化合物
反応式
CC1C(C(OC(C)(C)C)=O)CCC(Cl)C1.[CH3:16][CH2:17][O:18][C:19]([CH:21]1[CH:26]([CH3:27])[CH2:25][CH2:24][CH:23]([I:28])[CH2:22]1)=[O:20].C[C@H]1[C@H](C(O)=O)CC=CC1.CC1C(C(O)=O)CC=CC1>>[I:28][C@H:23]1[CH2:22][C@@H:21]([C:19]([O:18][CH2:17][CH3:16])=[O:20])[C@H:26]([CH3:27])[CH2:25][CH2:24]1参加物
5
実験手順
Test compounds: Liquid trimedlure (UOP Chemicals, East Rutherford, N.J.) (98% pure; density 1.02 g/ml) and ceralure (Agrisense/Biosys, Palo Alto, Calif.) (98% pure; density 1.43 g.ml) were purchased from commercial sources. The 2 g polymeric plug (Agrisense/Biosys, Palo Alto, Calif.) was the same product used by action agencies such as USDA-APHIS and California Department of Food and Agriculture (CDFA) in their surveillance and detection programs against medfly. The enantiomers of ceralure B1 (ethyl-cis-5-iodo-trans-2-methylcyclohexane-1-carboxylate) (henceforth referred to as the 1R,2R,5R and 1S,2S,5S enantiomers respectively) were synthesized using the 9 step process (described above) which yielded both enantiomers with high purity (97% ) and an overall yield of 15%. The racemic mixture of the two enantiomers was produced starting from racemic (5), which is (1RS, 6RS)-6-methyl-3-cyclohexene-1-carboxylic acid, using the above described process used to produce ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate (4a).