[(1S)-2-[2-(methoxymethoxy)ethyl]-1,3-dimethylcyclohex-2-en-1-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone | 179261-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [(1S)-2-[2-(methoxymethoxy)ethyl]-1,3-dimethylcyclohex-2-en-1-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone
• CAS: 179261-06-4
• 化学式: C₁₉H₃₃NO₄
• 分子量: 339.475
• InChiKey: KPQUOPRRPPNTHT-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S)-2-[2-(methoxymethoxy)ethyl]-1,3-dimethylcyclohex-2-en-1-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以84%的产率得到(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
• 作为产物：
  描述：

  (S)-(+)-2-(甲氧基甲基)吡唑烷 在 palladium on activated charcoal 三氯化铝 、 间戊二烯 、 氨 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 叔丁醇 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 137.5h， 生成 [(1S)-2-[2-(methoxymethoxy)ethyl]-1,3-dimethylcyclohex-2-en-1-yl]-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methanone
  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.