anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one) | 188782-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one)
• CAS: 188782-46-9
• 化学式: C₃₂H₃₀O₂
• 分子量: 446.589
• InChiKey: WJJKZHAKVQWUPW-RLQUZOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  34.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙二醇 、 anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one) 在 对甲苯磺酸 作用下， 以 硝基苯 、 苯 为溶剂， 反应 48.0h， 以60%的产率得到anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one)bis(ethyleneacetal)
  参考文献：
  名称：

  Bisacetals of aromatic ring-annelated . [3.3][3.3]Orthocyclophanes with triple-layered benzo/benzo/benzo- and naphtho/benzo/naphtho-system

  摘要：

  Tetraesters anti-9a,b and syn-9a,b, which have three aromatic rings, were prepared by the reaction of benzocycloheptenediester 7 with 1,2,4,5-tetrakis(bromomethyl)benzene. Subsequent hydrolysis and pyrolysis gave diketones anti-11a,b and syn-11a,b, which were acetalized to yield bisacetals anti-5a,b and syn-5a,b. X-Ray crystallographic analyses indicate a symmetric (twin-chair)/(twin-chair)-conformation of anti-5a,b, in which two naphtho or benzo rings sandwich one benzene ring. Anti-5a and anti-5b(9b)) are rigid structures. The protons of their central aromatic rings show an up-field shift, due to an anisotropic effect of the facing outer aromatic units. In contrast, syn-5a,b are flexible structures. The UV-spectra of anti-5a,b show a long wavelength shift, as compared to syn-5a,b, suggesting a through-space interaction among the aromatic rings. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00042-2
• 作为产物：
  描述：

  anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one)-6,10,17,21-tetracarboxylic acid 以65%的产率得到anti-benzo[1,2-h;4,5-h']bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one)
  参考文献：
  名称：

  Bisacetals of aromatic ring-annelated . [3.3][3.3]Orthocyclophanes with triple-layered benzo/benzo/benzo- and naphtho/benzo/naphtho-system

  摘要：

  Tetraesters anti-9a,b and syn-9a,b, which have three aromatic rings, were prepared by the reaction of benzocycloheptenediester 7 with 1,2,4,5-tetrakis(bromomethyl)benzene. Subsequent hydrolysis and pyrolysis gave diketones anti-11a,b and syn-11a,b, which were acetalized to yield bisacetals anti-5a,b and syn-5a,b. X-Ray crystallographic analyses indicate a symmetric (twin-chair)/(twin-chair)-conformation of anti-5a,b, in which two naphtho or benzo rings sandwich one benzene ring. Anti-5a and anti-5b(9b)) are rigid structures. The protons of their central aromatic rings show an up-field shift, due to an anisotropic effect of the facing outer aromatic units. In contrast, syn-5a,b are flexible structures. The UV-spectra of anti-5a,b show a long wavelength shift, as compared to syn-5a,b, suggesting a through-space interaction among the aromatic rings. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00042-2

文献信息

• Benzo[3.3]benzo[3.3]benzo- and naphtho[3.3]benzo[3.3]naphtho-orthocyclophane bis(alcohol)s. Preparations and structures
  作者：Shuntaro Mataka、Yoshiharu Mitoma、Tsuyoshi Sawada、Thies Thiemann、Masahiko Taniguchi、Masashi Tashiro

  DOI：10.1016/s0040-4020(98)00217-8

  日期：1998.5

  anti-Benzo[1,2-h;4,5-h′]bis(benzo[1,2-c]bicyclo[4.4.1]undeca-3,8-diene-11-one) (7a and bis(naphtho[2,3-c]bicyclo[4.4.1]undeca-3,8-diene-11-one) derivative 7b reacted with Grignard reagents (MeMgI and PhMgBr) to give bis(alcohol)s 10–12 or monoalcohols 13 and 14, depending upon the amount of the reagent used. Similarly, syn-bis(alcohol)s 15–17 and syn-monoalcohols 18 and 19 were obtained in the reaction

  抗-苯并[1,2- h ; 4,5- h ']双（苯并[1,2- c ]双环[4.4.1] undeca-3,8-二烯-11-one）（7a和bis（萘并[2,3- c ]双环[4.4.1] undeca-3,8-二烯-11-one）衍生物7b与格氏试剂（MeMgI和PhMgBr）反应，生成双（醇）10-12或一元醇13和14，这取决于所使用的试剂的量。类似地，顺式-双（醇）15-17和SYN -monoalcohols 18和19中的反应制得顺式-苯并[1,2 ħ； 4，5- h ′]双（苯并[1,2- c ]双环[4.4.1] undeca-3,8-二烯-11-one）（9）与格利雅试剂。生成的10–19醇为构型异构体的混合物，每种异构体均通过HPLC分离。通过1 H和13 C NMR光谱，NOE研究以及12a，13和17a的X射线晶体学分析确定结构。三层[3.3] [3.3]原环烷酮