11-chloro-9,10-dihydro-9,10-ethenoanthracene | 6226-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-chloro-9,10-dihydro-9,10-ethenoanthracene
• 英文别名: 11-chloro-9,10-dihydro-9,10-etheno-anthracene；11-Chlor-9,10-dihydro-9,10-aetheno-anthracen；7-Chlorodibenzobicyclo-<2.2.2>-octatrien；7-Chlor-dibenzocyclo<2.2.2>octatrien；15-chlorotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene
• CAS: 6226-22-8
• 化学式: C₁₆H₁₁Cl
• 分子量: 238.716
• InChiKey: SYZTYABTKLVWAU-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C(Solv: methanol (67-56-1))
• 沸点：
  363.2±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  11-chloro-9,10-dihydro-9,10-ethenoanthracene 生成 9,10-二氢-9,10-乙烯桥蒽
  参考文献：
  名称：

  Bridged Polycyclic Compounds. XXIX. Some Rearrangements of Dibenzobicyclo[2.2.2]octadienes to Dibenzobicyclo[3.2.1]octadienes¹

  摘要：

  DOI：

  10.1021/ja01091a017
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 11-chloro-9,10-dihydro-9,10-ethenoanthracene
  参考文献：
  名称：

  Mechanisms of Elimination Reactions. V. Preparation and Elimination Reactions of cis- and trans-11,12-Dichloro-9,10-dihydro-9,10-ethanoanthracene^{1,2, 3}

  摘要：

  DOI：

  10.1021/ja01129a013

文献信息

• Generalization of the triptycene concept. Use of diaryne equivalents in the synthesis of iptycenes
  作者：Harold Hart、Shamouil Shamouilian、Yoshikazu Takehira

  DOI：10.1021/jo00335a021

  日期：1981.10
• Bridged Polycyclic Compounds. XXXVII. Addition of Benzenesulfenyl Chloride and Bromine to 7-Chlorodibenzobicyclo [2.2.2]octatriene¹
  作者：Stanley J. Cristol、Bruce B. Jarvis

  DOI：10.1021/ja00965a037

  日期：1966.7
• Bridged Polycyclic Compounds. XXXIV. Acetolysis of cis- and trans-β-Chlorodibenzobicyclo[2.2.2]octadienyl Thioethers¹
  作者：Stanley J. Cristol、Ronald Caple、R. M. Sequeira、L. Oliver Smith

  DOI：10.1021/ja00952a028

  日期：1965.12
• Stereoselective free-radical rearrangements
  作者：Bruce B. Jarvis、John P. Govoni、Philip J. Zell

  DOI：10.1021/ja00733a020

  日期：1971.2
• Synthesis of supertriptycene and two related iptycenes
  作者：Khalil Shahlai、Harold Hart

  DOI：10.1021/jo00024a037

  日期：1991.11

  A 10-step 23-30% overall yield synthesis of supertriptycene (2) from vinyl chloride 5 is described. Anthracene 3 is the key intermediate, prepared from 5 in six steps and 41-53% yield (Scheme II). trans-1,2-Dichloroethene adds to 3 to give adduct 22 (94%), which is then converted to 2 in three steps and 70% yield (Scheme IV). A key step in the latter sequence is the remarkable cycloaddition of unactivated alkene 26 to hindered diene 4 in excellent yield. Supertriptycene (2), C104H62, shows only seven peaks in its H-1 NMR spectrum and 12 peaks in its C-13 NMR spectrum, consistent with its D3h symmetry. The hydrocarbon is stable to well over 500-degrees-C. Anthracene 3 was also converted to undecaiptycene 12 and to tridecaiptycene 16; the latter was also independently synthesized in two steps from alkene 26 and diene 28.