1-(m-biphenylyl)-2-phenylethyne | 263916-95-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-(m-biphenylyl)-2-phenylethyne
• 英文别名: 3-phenyldiphenylacetylene；3-(phenylethynyl)-1,1'-biphenyl；1-Phenyl-3-(2-phenylethynyl)benzene
• CAS: 263916-95-6
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: IKFCFSGZUBUKFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  1-(m-biphenylyl)-2-phenylethyne 在 四丁基氢氧化铵 、 碘 、 二甲基亚砜 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 18.25h， 生成 2,5-bis(3,5-diphenylphenyl)-3-phenyl-4-(3-biphenyl)cyclopentadienone
  参考文献：
  名称：

  大型多环芳烃的合成：尺寸和周边的变化

  摘要：

  通过合适的低聚亚苯基前体在温和条件下的氧化环化脱氢，合成了一系列具有不同外围的新系列多环芳烃（PAHs）。如此大的多环芳烃被认为是二维石墨截面，其电子特性有望收敛于宏观石墨的电子特性。低聚亚苯基骨架的合成构建主要基于 Diels-Alder 反应或环三聚反应。它们随后被转化为含有多达 78 个碳原子的平面芳烃。由于扩展多环芳烃的溶解度不足，通过激光解吸/电离飞行时间质谱和薄膜的紫外/可见光谱进行表征。

  DOI：

  10.1021/ja000832x
• 作为产物：
  描述：

  (E)-3-(2-phenylethenyl)-1,1'-biphenyl 在 potassium tert-butylate 、 溴 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 8.0h， 生成 1-(m-biphenylyl)-2-phenylethyne
  参考文献：
  名称：

  The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums

  摘要：

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01090-x

文献信息

• Transition-Metal-Free Alkynylation of Aryl Chlorides
  作者：Thanh Truong、Olafs Daugulis

  DOI：10.1021/ol2014736

  日期：2011.8.19

  Two sets of conditions have been developed for a base-mediated, transition-metal-free alkynylation of aryl chlorides that proceeds via benzyne intermediates. The first set of conditions Involves the use of TMPLI base in a pentane/THF mixture at 25 degrees C. The second set Involves use of a metal alkoxide base in dioxane at elevated temperature. Reasonable functional group tolerance has been observed. Fluoro, trifluoromethyl, silyl, cyano, and alcohol functionalities are compatible with the reaction conditions.
• Synthesis of Large Polycyclic Aromatic Hydrocarbons:  Variation of Size and Periphery
  作者：Florian Dötz、Johann Diedrich Brand、Shunji Ito、Lileta Gherghel、Klaus Müllen

  DOI：10.1021/ja000832x

  日期：2000.8.1

  series of polycyclic aromatic hydrocarbons (PAHs) with different peripheries was synthesized via oxidative cyclodehydrogenation of suitable oligophenylene precursors under mild conditions. Such large PAHs are considered to be two-dimensional graphite sections whose electronic properties are expected to converge to those of macroscopic graphite. The synthetic buildup of the oligophenylene frameworks

  通过合适的低聚亚苯基前体在温和条件下的氧化环化脱氢，合成了一系列具有不同外围的新系列多环芳烃（PAHs）。如此大的多环芳烃被认为是二维石墨截面，其电子特性有望收敛于宏观石墨的电子特性。低聚亚苯基骨架的合成构建主要基于 Diels-Alder 反应或环三聚反应。它们随后被转化为含有多达 78 个碳原子的平面芳烃。由于扩展多环芳烃的溶解度不足，通过激光解吸/电离飞行时间质谱和薄膜的紫外/可见光谱进行表征。
• The First Aryne Evolution from the Reactions of Selenonium Salts with Aryllithiums
  作者：Shin-ichi Watanabe、Keiichirou Yamamoto、Yukiko Itagaki、Tatsunori Iwamura、Tetsuo Iwama、Tadashi Kataoka

  DOI：10.1016/s0040-4020(99)01090-x

  日期：2000.2

  The first example of the benzyne generation was found in the reactions of alkynylselenonium salt 1a with 1.0 equiv. of phenyllithium in THF at room temperature for 3 h. The formation of the aryne intermediate was confirmed in the reactions of alkynylselenonium salt 1b and tri-p-tolylselenonium salt 6b with tolyllithium, which gave a mixture of alkynylbiphenyl derivatives 18 and 19 in 19% yield (18:19=11:8) and a mixture of bitolyls 28 and 29 in 63% yield (28:29=2:1), respectively. The reaction mechanisms of these reactions are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.