(S)-5,8a-Dimethyl-3,4,6,7,8,8a-hexahydro-isochromen-1-one | 179261-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-5,8a-Dimethyl-3,4,6,7,8,8a-hexahydro-isochromen-1-one
• 英文别名: (8aS)-5,8a-dimethyl-4,6,7,8-tetrahydro-3H-isochromen-1-one
• CAS: 179261-07-5
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: HLZXPPUEKWUIBL-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5,8a-Dimethyl-3,4,6,7,8,8a-hexahydro-isochromen-1-one 、 原甲酸三甲酯 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以86%的产率得到(1S)-1,3-dimethyl-2-(2-methoxyethyl)-2-cyclohexene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Caribbean Fruit Fly Pheromone (+)-Epianastrephin

  摘要：

  An asymmetric total synthesis of (+)-epianastrephin (1) from the chiral benzamide 2 (15 steps, 9.5% overall yield) is described. Birch reduction-alkylation of 2 with methyl iodide gave 3 in 91% yield as a single diastereomer. Cyclohexadiene 3 was converted to olefinic carboxylic acid 6b, and a tandem iodolactonization-radical reduction sequence provided lactone 8 with three contiguous stereogenic centers. Chiral HPLC comparison of diol 12b, the immediate precursor to (+)epianastrephin (1), with 12b prepared from racemic epianastrephin demonstrated that 1 had been prepared with > 98% ee.

  DOI：

  10.1021/jo960568j
• 作为产物：
  描述：

  [(1S)-2-[2-(methoxymethoxy)ethyl]-1,3-dimethylcyclohexa-2,5-dien-1-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 144.0h， 生成 (S)-5,8a-Dimethyl-3,4,6,7,8,8a-hexahydro-isochromen-1-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Caribbean Fruit Fly Pheromone (+)-Epianastrephin

  摘要：

  An asymmetric total synthesis of (+)-epianastrephin (1) from the chiral benzamide 2 (15 steps, 9.5% overall yield) is described. Birch reduction-alkylation of 2 with methyl iodide gave 3 in 91% yield as a single diastereomer. Cyclohexadiene 3 was converted to olefinic carboxylic acid 6b, and a tandem iodolactonization-radical reduction sequence provided lactone 8 with three contiguous stereogenic centers. Chiral HPLC comparison of diol 12b, the immediate precursor to (+)epianastrephin (1), with 12b prepared from racemic epianastrephin demonstrated that 1 had been prepared with > 98% ee.

  DOI：

  10.1021/jo960568j

文献信息

• Asymmetric Total Synthesis of the Caribbean Fruit Fly Pheromone (+)-Epianastrephin
  作者：Arthur G. Schultz、Steven J. Kirincich

  DOI：10.1021/jo960568j

  日期：1996.1.1

  An asymmetric total synthesis of (+)-epianastrephin (1) from the chiral benzamide 2 (15 steps, 9.5% overall yield) is described. Birch reduction-alkylation of 2 with methyl iodide gave 3 in 91% yield as a single diastereomer. Cyclohexadiene 3 was converted to olefinic carboxylic acid 6b, and a tandem iodolactonization-radical reduction sequence provided lactone 8 with three contiguous stereogenic centers. Chiral HPLC comparison of diol 12b, the immediate precursor to (+)epianastrephin (1), with 12b prepared from racemic epianastrephin demonstrated that 1 had been prepared with > 98% ee.