benzo<2.2>metaparacyclophan-9-ene | 82733-10-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: benzo<2.2>metaparacyclophan-9-ene
• 英文别名: Benzo<2.2>metaparacyclophan-9-en；(13Z)-tetracyclo[13.2.2.18,12.02,7]icosa-1(17),2,4,6,8,10,12(20),13,15,18-decaene
• CAS: 82733-10-6
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: WVFNKLLCEGAFSG-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  benzo<2.2>metaparacyclophan-9-ene 在 potassium tert-butylate 、 溴 作用下， 以 四氯化碳 为溶剂， 生成 1,4-dihydro-1,4-endoxo-14,17-etheno-5,9-methenodibenzocyclotridecene
  参考文献：
  名称：

  Wong, Timothy; Cheung, Siu Shing; Wong, Henry N.C., Angewandte Chemie, 1988, vol. 100, # 5, p. 716 - 717

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzo<2.2>metaparacyclophan 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium tert-butylate 作用下， 生成 benzo<2.2>metaparacyclophan-9-ene
  参考文献：
  名称：

  Wong, Timothy; Cheung, Siu Shing; Wong, Henry N.C., Angewandte Chemie, 1988, vol. 100, # 5, p. 716 - 717

  摘要：

  DOI：

文献信息

• Wong, Timothy; Cheung, Siu Shing; Wong, Henry N.C., Angewandte Chemie, 1988, vol. 100, # 5, p. 716 - 717
  作者：Wong, Timothy、Cheung, Siu Shing、Wong, Henry N.C.

  DOI：——

  日期：——
• Arene synthesis by extrusion reaction. 15. Synthesis and conformational behavior of benzo[2.2]metaparacyclophan-9-ene, dibenzo[2.2]metaparacyclophane and 1,4-dimethyldibenzo[2.2]metaparacyclophane. X-ray crystal structure of dibenzo[2.2]metaparacyclophane
  作者：Timothy Wong、Mabel S. M. Yuen、Thomas C. W. Mak、Henry N. C. Wong

  DOI：10.1021/jo00063a035

  日期：1993.5

  Dibenzo[2.2]metaparacyclophane (5) and its 1,4-dimethyl derivative 6 have been synthesized utilizing low-valent-titanium deoxygenation as the key step. The conformational mobility of 5 and 6, as well as that of benzo[2.2]metaparacyclophane (3) and benzo[2.2]metaparacyclophan-9-ene (4) have been studied by variable temperature NMR spectrometry. The results of this study, together with those reported for [2.2]metaparacyclophane (1) and [2.2]metaparacyclophane-1,9-diene (2), show that the free energy of activation for the flipping process (DELTAG(c)double dagger) at the coalescence temperature (T(c)) is closely related to the bond types of the bridges connecting the meta-bridged benzenes and the para-linked ones. In addition to these structural effects, the nonbonded interactions of H-1 and H15, and that of H12 with H13 in 5 also influence such conformational behavior, as can be unequivocally substantiated by the synthesis and study of 6. An X-ray crystallographic study has shown that 5 conforms closely to idealized C(s) molecular symmetry with a dihedral angle of 147.2-degrees between the pair of orthobenzenes and a pronounced boat conformation for the para-bridged one.