(2Z,8E,10Z)-3-methyl-15-oxabicyclo[9.3.2]hexadeca-2,8,10-triene | 1248573-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (2Z,8E,10Z)-3-methyl-15-oxabicyclo[9.3.2]hexadeca-2,8,10-triene
• CAS: 1248573-68-3
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: YKZCWYLUOVLUTI-CWHRVQFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z,8E,10Z)-3-methyl-15-oxabicyclo[9.3.2]hexadeca-2,8,10-triene 以 甲苯 为溶剂， 反应 4.0h， 以100%的产率得到(+/-)-(4R,4aS,4bS,8aR,10aR)-4,10a-(epoxymethylene)-4b-methyl-1,2,3,4,4a,4b,5,6,7,8, 8a,10a-dodecahydrophenanthrene
  参考文献：
  名称：

  Synthesis of a trans,syn,trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels−Alder Reaction: Intermediate for the Synthesis of Fusidic Acid

  摘要：

  While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13. heating the corresponding ether 18 to 110 degrees C for 4 h afforded a quantitative yield ol the desired cycloadduct 19. which could be easily reduced to the perhydrophenanthrene. an ABC ring analogue of lusidic acid 1 Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does

  DOI：

  10.1021/jo101533h
• 作为产物：
  描述：

  (2Z,8E,10Z)-11-(hydroxymethyl)-3-methylcyclotetradeca-2,8,10-trienol 在 三光气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以65%的产率得到(2Z,8E,10Z)-3-methyl-15-oxabicyclo[9.3.2]hexadeca-2,8,10-triene
  参考文献：
  名称：

  Synthesis of a trans,syn,trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels−Alder Reaction: Intermediate for the Synthesis of Fusidic Acid

  摘要：

  While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13. heating the corresponding ether 18 to 110 degrees C for 4 h afforded a quantitative yield ol the desired cycloadduct 19. which could be easily reduced to the perhydrophenanthrene. an ABC ring analogue of lusidic acid 1 Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does

  DOI：

  10.1021/jo101533h