(1R,4S,4aR,5S,5aS,6R,11S,11aR,12R,12aS)-1,4,4a,5,5a,6,11,11a,12,12a-decahydro-1,4:5,12:6,11-triepoxytetracene | 879213-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,4S,4aR,5S,5aS,6R,11S,11aR,12R,12aS)-1,4,4a,5,5a,6,11,11a,12,12a-decahydro-1,4:5,12:6,11-triepoxytetracene
• CAS: 879213-03-3
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: FQWQYRVPIQJXGD-VUGFDTLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,5S,5aS,6R,11S,11aR,12R,12aS)-1,4,4a,5,5a,6,11,11a,12,12a-decahydro-1,4:5,12:6,11-triepoxytetracene 、 2,5-二(三氟甲基)-1,3,4-恶二唑 以 二氯甲烷 为溶剂， 反应 0.75h， 以11%的产率得到1,20-bis(trifluoromethyl)-(1α,2β,3α,4β,5α,6α,7β,14β,15α,16α,17β,18α,19β,20α,21α,22β,23α,24β,25β,26α,33α,34β,35β,36α,37β,38α)-39,40,41,42,43,44,45-heptaoxahexadecacyclo[18.18.1.1(3,18).1(5,16).1(7,14).1(22,37).1(24,35).1(26,33).0(2,19).0(4,17).0(6,15).0(8,13).0(21,38).0(23,36).0(25,34).0(27,32)]pentatetraconta-8,10,12,27,29,31-hexaene
  参考文献：
  名称：

  Reaction of 2,5-bis-trifluoromethyl-1,3,4-oxadiazole with 7-oxanorbornenes revisited: Experimental and quantum-chemical study of reaction stereoselectivity

  摘要：

  The stereochemical outcome of reaction of 2,5-bis-trifluoromethyl-1,3,4-oxadiazole with 7-oxanorbornenes under various conditions was investigated. For the first time, microwave irradiation in carrying this type of reactions was used, resulting in comparable yields in significantly shorter reaction times. Regardless on substrate, in all reactions mixtures of the two isomeric O-3-[3]polynorbornanes, bent and linear were obtained, with slight preference for bent structure. In some cases, retro Diels-Alder fragmentation was observed resulting in formation of isobenzofuran species. Reaction mechanism was also studied computationally (RHF/6-31G* method), and the origin of stereoselectivity explained by repulsive lone pair interactions between oxygen bridges in the transition state of the 1,3-dipolar addition. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.12.012