Dimethyl 1,2,3,4,5,6,7,8-octahydrophenanthrene-9,10-dicarboxylate | 51037-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Dimethyl 1,2,3,4,5,6,7,8-octahydrophenanthrene-9,10-dicarboxylate
• CAS: 51037-17-3
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: QIFIEWSYIZHSQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Dimethyl tetracyclo<10.2.0.0^1,6.0^7,12>tetradeca-6,13-diene-13,14-dicarboxylate 以 乙醚 为溶剂， 反应 3.0h， 生成 Dimethyl 1,2,3,4,5,6,7,8-octahydrophenanthrene-9,10-dicarboxylate
  参考文献：
  名称：

  Synthesis of doubly bridged prismanes: an investigation of the photochemical behavior of doubly bridged Dewar benzenes

  摘要：

  Starting from cyclic acetylenes, two stereoisomeric doubly bridged Dewar benzenes of type 14 and 15 were synthesized, and the effects of the chain length and the nature of two other functional groups on their photochemical behavior were examined. The isomers with bridges spanning the 1,4- and 2,3-positions, 14b,c and 25b, reacted to form the respective prismanes, 17b,c and 27b. Isomers 15b-d, with bridges spanning the 1,2- and 3,4-positions, revealed a more complex photochemistry. through consecutive transposition reactions via a total of five intermediates, an unexpected phthalic/terephthalic ester rearrangement was observed. Prismane 38b and Dewar benzenes 39b,c could be characterized directly, and the existence of the other intermediates was deduced indirectly.

  DOI：

  10.1021/jo00079a019

文献信息

• Gleiter, Rolf; Kratz, Detlev, Angewandte Chemie, 1990, vol. 102, # 3, p. 304 - 307
  作者：Gleiter, Rolf、Kratz, Detlev

  DOI：——

  日期：——
• Courtot,P.; Clement,J.-C., Bulletin de la Societe Chimique de France, 1973, p. 2121 - 2125
  作者：Courtot,P.、Clement,J.-C.

  DOI：——

  日期：——
• Gleiter, Rolf; Treptow, Bjoern, Angewandte Chemie, 1992, vol. 104, # 7, p. 879 - 881
  作者：Gleiter, Rolf、Treptow, Bjoern

  DOI：——

  日期：——
• Synthesis of doubly bridged prismanes: an investigation of the photochemical behavior of doubly bridged Dewar benzenes
  作者：Rolf Gleiter、Bjoern Treptow

  DOI：10.1021/jo00079a019

  日期：1993.12

  Starting from cyclic acetylenes, two stereoisomeric doubly bridged Dewar benzenes of type 14 and 15 were synthesized, and the effects of the chain length and the nature of two other functional groups on their photochemical behavior were examined. The isomers with bridges spanning the 1,4- and 2,3-positions, 14b,c and 25b, reacted to form the respective prismanes, 17b,c and 27b. Isomers 15b-d, with bridges spanning the 1,2- and 3,4-positions, revealed a more complex photochemistry. through consecutive transposition reactions via a total of five intermediates, an unexpected phthalic/terephthalic ester rearrangement was observed. Prismane 38b and Dewar benzenes 39b,c could be characterized directly, and the existence of the other intermediates was deduced indirectly.