Dimethyl tetracyclo<12.2.0.0^1,7.0^8,14>hexadeca-7,15-diene-15,16-dicarboxylate | 130434-04-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dimethyl tetracyclo<12.2.0.0^1,7.0^8,14>hexadeca-7,15-diene-15,16-dicarboxylate
• 英文别名: Dimethyl tetracyclo[9.5.0.01,4.04,10]hexadeca-2,10-diene-2,3-dicarboxylate
• CAS: 130434-04-7
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: YBBZUOYJFWRFGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl tetracyclo<12.2.0.0^1,7.0^8,14>hexadeca-7,15-diene-15,16-dicarboxylate 以 乙醚 为溶剂， 反应 3.0h， 生成 Dimethyl 1,2,3,4,5,8,9,10,11,12-decahydrobenzo<1,2:3,4>biscycloheptene-6,7-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
• 作为产物：
  描述：

  1,8-环十四二炔 、 丁炔二酸二甲酯 在 三氯化铝 、 二甲基亚砜 作用下， 生成 Dimethyl tetracyclo<7.5.2.0.0^2,8>hexadeca-2,15-diene-15,16-dicarboxylate 、 Dimethyl tetracyclo<12.2.0.0^1,7.0^8,14>hexadeca-7,15-diene-15,16-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; Treptow, Bjoern, Angewandte Chemie, 1990, vol. 102, # 12, p. 1452 - 1454
  作者：Gleiter, Rolf、Treptow, Bjoern

  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：——
• GLEITER, ROLF;TREPTOW, BJORN, ANGEW. CHEM., 102,(1990) N2, C. 1452-1454
  作者：GLEITER, ROLF、TREPTOW, BJORN

  DOI：——

  日期：——
• Gleiter, Rolf; Ohlbach, Frank; Oeser, Thomas, Liebigs Annalen, 1996, # 5, p. 785 - 790
  作者：Gleiter, Rolf、Ohlbach, Frank、Oeser, Thomas、Irngartinger, Hermann

  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.