exo-endo-1,4:9,10-diepoxy-1,4,4a,9,9a,10-hexahydroanthracene | 38648-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: exo-endo-1,4:9,10-diepoxy-1,4,4a,9,9a,10-hexahydroanthracene
• CAS: 38648-97-4
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: MUCFYYOZGBBVHR-XUYNTYLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  exo-endo-1,4:9,10-diepoxy-1,4,4a,9,9a,10-hexahydroanthracene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以92%的产率得到exo-endo-1,4:9,10-diepoxy-1,2,3,4,4a,9,9a,10-octahydroanthracene
  参考文献：
  名称：

  Long-range interaction between lone-pair orbitals in diepoxynaphthalene derivatives

  摘要：

  DOI：

  10.1021/jo00011a052

文献信息

• High Pressure Synthesis of New Silicon Containing Heteroatom Analogues of Fused Norbornenes
  作者：Srécko I. Kirin、Frank-Gerrit Klärner、Mirjana Eckert-Maksić

  DOI：10.1055/s-1999-2596

  日期：1999.3

  The synthesis of fused norbornene analogues containing silicon and oxygen atoms in bridgehead positions is reported. This novel type of compound can be readily obtained in stereospecific Diels-Alder [4+2] cycloaddition of siloles with oxanorbornene derivatives as appropriate dienophiles by the use of high pressure (9 kbar).

  报道了在桥头位置含有硅和氧原子的稠合降冰片烯类似物的合成。这种新型化合物可以通过使用高压（9 kbar），通过噻咯与作为合适的亲二烯体的氧杂降冰片烯衍生物的立体特异性狄尔斯-阿尔德[4+2]环加成反应容易地获得。
• 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.