9,10-bis(2-chlorophenyl)phenanthrene

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 9,10-bis(2-chlorophenyl)phenanthrene
• 英文别名: anti-9,10-Bis(2-chlorophenyl)phenanthrene
• 化学式: C₂₆H₁₆Cl₂
• 分子量: 399.319
• InChiKey: IQURMRZDECZNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  2
• 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

• 作为产物：
  描述：

  1,2-bis-(2-chloro-phenyl)-1,2-diphenyl-ethane-1,2-diol 在 三氟甲磺酸 作用下， 反应 8.0h， 以100%的产率得到9,10-bis(2-chlorophenyl)phenanthrene
  参考文献：
  名称：

  Preparation of Condensed Aromatics by Superacidic Dehydrative Cyclization of Aryl Pinacols and Epoxides^1a

  摘要：

  Aryl pinacols and epoxides, respectively, are cleanly and in high yield converted via superacidic dehydrative cyclization to the corresponding condensed aromatics. Dehydrative cyclization of benzopinacol (1a), triphenylacetophenone (2), and tetraphenylethylene oxide (9) give 9,10-diphenylphenanthrene (3a) as the major product in acidic media stronger than H-o = -11. Aryl pinacol 12a forms the condensed aromatic 13a as the major product in acidic media stronger than H-o = -13.5. It is proposed that the dehydrative cyclizations to provide aromatics 3a and 13a occurs through dicationic intermediates. Substituted benzopinacols 1f, 1g, and 1j are prepared and give the corresponding phenanthrenes (3f, 3g, and 3j) in high yields. The regiochemistry of the cyclization of substituted benzopinacols is controlled by deactivating substituents on the aryl rings. Aryl pinacols (12a-d) derived from acenaphthenequinone and pinacol 15 also give condensed aromatics (13a-d and 16, repectively) with superacidic triflic acid.

  DOI：

  10.1021/jo970293n

文献信息

• Rotation of Aryl Groups in 9,10-Diarylphenanthrenes: Does the Rotational Barrier Become Lower as the Backbone Becomes More Crowded?
  作者：Jen-Yi Li、Hung-Ing Chang、Chieh-Ning Feng、Yao-Ting Wu

  DOI：10.1021/acs.orglett.6b03343

  日期：2016.12.16

  was prepared, and their structures and dynamic behaviors were both theoretically and experimentally investigated. A more twisted and crowded phenanthrene backbone was associated with a lower barrier to the rotation of an aryl group.

  制备了一系列的9,10-二芳基菲，并对其结构和动力学行为进行了理论和实验研究。菲骨架更扭曲和拥挤与芳基旋转的较低障碍相关。
• Preparation of Condensed Aromatics by Superacidic Dehydrative Cyclization of Aryl Pinacols and Epoxides¹^a
  作者：Douglas A. Klumpp、Donald N. Baek、G. K. Surya Prakash、George A. Olah

  DOI：10.1021/jo970293n

  日期：1997.9.1

  Aryl pinacols and epoxides, respectively, are cleanly and in high yield converted via superacidic dehydrative cyclization to the corresponding condensed aromatics. Dehydrative cyclization of benzopinacol (1a), triphenylacetophenone (2), and tetraphenylethylene oxide (9) give 9,10-diphenylphenanthrene (3a) as the major product in acidic media stronger than H-o = -11. Aryl pinacol 12a forms the condensed aromatic 13a as the major product in acidic media stronger than H-o = -13.5. It is proposed that the dehydrative cyclizations to provide aromatics 3a and 13a occurs through dicationic intermediates. Substituted benzopinacols 1f, 1g, and 1j are prepared and give the corresponding phenanthrenes (3f, 3g, and 3j) in high yields. The regiochemistry of the cyclization of substituted benzopinacols is controlled by deactivating substituents on the aryl rings. Aryl pinacols (12a-d) derived from acenaphthenequinone and pinacol 15 also give condensed aromatics (13a-d and 16, repectively) with superacidic triflic acid.