1,12-bis(trifluoromethyl)-(1α,2α,3β,10β,11α,12α,13β,14α,21α,22β)-23,24,25-trioxaoctacyclo[10.10.1.1(3,10).1(14,21).0(2,11).0(4,9).0(13,22).0(15,20)]pentacosa-4,6,8,15,17,19-hexaene | 134842-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,12-bis(trifluoromethyl)-(1α,2α,3β,10β,11α,12α,13β,14α,21α,22β)-23,24,25-trioxaoctacyclo[10.10.1.1(3,10).1(14,21).0(2,11).0(4,9).0(13,22).0(15,20)]pentacosa-4,6,8,15,17,19-hexaene
• CAS: 134842-35-6
• 化学式: C₂₄H₁₆F₆O₃
• 分子量: 466.38
• InChiKey: DOCMCHBZZWUKPX-XWZDVXJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  33.0
• 可旋转键数：
  0.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,4-二氢-1,4-环氧萘 、 2,5-二(三氟甲基)-1,3,4-恶二唑 以 二氯甲烷 为溶剂， 生成 1,12-bis(trifluoromethyl)-(1α,2α,3β,10β,11α,12α,13β,14α,21α,22β)-23,24,25-trioxaoctacyclo[10.10.1.1(3,10).1(14,21).0(2,11).0(4,9).0(13,22).0(15,20)]pentacosa-4,6,8,15,17,19-hexaene
  参考文献：
  名称：

  The 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Coupling of Norbornenes and 7-Oxanorbornenes under High Pressure: New Structures, Mechanistic Detail and Synthetic Applications

  摘要：

  在双环烯烃与 1,3,4-恶二唑（和 1,3,4-噻二唑）偶联的研究中使用了反应性、位点选择性、计算以及热与高压（14 kbar）反应条件的比较，其中设置这种耦合的边界条件并确定 1,3-偶极物质作为可能的中间体。

  DOI：

  10.1055/s-1997-738

文献信息

• The synthesis of polarofacial spacer molecules: a new twist in the coupling of ring strained olefins with oxadiazoles.
  作者：Ronald N. Warrener、Douglas N. Butler、Wen Yan Liao、Ian G. Pitt、Richard A. Russell

  DOI：10.1016/s0040-4039(00)85989-4

  日期：1991.4

  New approaches to the synthesis of rigid spacer molecules in which an oxygen-bridge bestows the facial polarity is described: attempts to couple 7-oxanorbornenes together using 1,3,4-oxadiazoles yields inverted, non linear products in a stereospecific reaction which differs significantly from that known to obtain with norbornenes.
• Reaction of 2,5-bis-trifluoromethyl-1,3,4-oxadiazole with 7-oxanorbornenes revisited: Experimental and quantum-chemical study of reaction stereoselectivity
  作者：Davor Margetić、Mirjana Eckert-Maksić、Pavle Trošelj、Željko Marinić

  DOI：10.1016/j.jfluchem.2009.12.012

  日期：2010.3

  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.