(1R,3S,5R,6R)-O-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-yl S-methyldithiocarbonate | 409313-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S,5R,6R)-O-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-yl S-methyldithiocarbonate
• 英文别名: O-[(1R,3S,5R,6R)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-yl] methylsulfanylmethanethioate
• CAS: 409313-48-0
• 化学式: C₁₂H₁₈O₃S₂
• 分子量: 274.405
• InChiKey: LGHCAUFSSYQBJW-BTQIBKBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  85.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S,5R,6R)-O-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-yl S-methyldithiocarbonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以44%的产率得到(1R,3S,5S)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene
  参考文献：
  名称：

  Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth, Endoclita excrescens, and Its Enantiomer

  摘要：

  The (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized from the (S)- and (R)-isomers of ethyl 3-hydroxybutanoate. The (1 R,3S,5S)-isomer was identified as the pheromone produced by the male Japanese hepialid moth, Endoclita excrescens. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200212)2002:23<3974::aid-ejoc3974>3.0.co;2-z
• 作为产物：
  描述：

  (1R,3S,5R,6R)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-ol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (1R,3S,5R,6R)-O-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-yl S-methyldithiocarbonate
  参考文献：
  名称：

  Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth, Endoclita excrescens, and Its Enantiomer

  摘要：

  The (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized from the (S)- and (R)-isomers of ethyl 3-hydroxybutanoate. The (1 R,3S,5S)-isomer was identified as the pheromone produced by the male Japanese hepialid moth, Endoclita excrescens. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200212)2002:23<3974::aid-ejoc3974>3.0.co;2-z

文献信息

• Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth, Endoclita excrescens, and Its Enantiomer
  作者：Kaoru Marukawa、Kenji Mori

  DOI：10.1002/1099-0690(200212)2002:23<3974::aid-ejoc3974>3.0.co;2-z

  日期：2002.12

  The (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized from the (S)- and (R)-isomers of ethyl 3-hydroxybutanoate. The (1 R,3S,5S)-isomer was identified as the pheromone produced by the male Japanese hepialid moth, Endoclita excrescens. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)