(1R,3S,5R,6R)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-ol | 409313-37-7

• 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)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-ol
• CAS: 409313-37-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: QIXBAZQQSNQFPS-SGIHWFKDSA-N

物化性质

• 沸点：
  274.2±40.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (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)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以94%的产率得到(1R,3S,5R,6R)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-ol
  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)