2-(phenylethynyl)-4,4'-dimethyl-1,1'-biphenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(phenylethynyl)-4,4'-dimethyl-1,1'-biphenyl
• 英文别名: 4,4'-dimethyl-2-(phenylethynyl)biphenyl；4-Methyl-1-(4-methylphenyl)-2-(2-phenylethynyl)benzene
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: HOFRCWYKVCPWQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2-(phenylethynyl)-4,4'-dimethyl-1,1'-biphenyl 在 manganese(IV) oxide 、 palladium dichloride 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.5h， 以71%的产率得到1,2-bis(2,7-dimethyl-9H-fluoren-9-ylidene)-1,2-diphenylethane
  参考文献：
  名称：

  FeCl3介导的二芴基二芳基乙烷的氧化螺环化导致双螺[芴-9,5'-茚并[2,1-a]茚-10-10,9''芴] s

  摘要：

  一种新型的FeCl 3介导的氧化螺环化反应，用于构建新型的双螺链连接的π共轭分子，即双螺[芴-9,5'-茚并[2,1- a ]茚10-10,9'-芴] s（DSFIIFs），已被报道。FeCl 3与FeO（OH）的结合引发了二芴基二芳基乙烷的前所未有的双单电子​​氧化，从而以高收率提供了相应的二螺环。溶液中的最高荧光量子产率高达0.94。该方案也适用于非螺旋连接的二氢茚并茚的合成。

  DOI：

  10.1002/anie.201507794
• 作为产物：
  描述：

  三苯基苄基溴化膦 在 溴 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-(phenylethynyl)-4,4'-dimethyl-1,1'-biphenyl
  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

• Gold-catalyzed efficient tandem assembly of terminal alkynes and arynes: synthesis of alkynylated biphenyl derivatives
  作者：Chunsong Xie、Yuhong Zhang、Yuzhu Yang

  DOI：10.1039/b806821f

  日期：——

  Gold catalysts have been found to catalyze the tandem assembly of arynes and terminal alkynes efficiently in the presence of CuI under mild reaction conditions to provide useful alkynylated biphenyl derivatives.

  已经发现，在CuI的存在下，在温和的反应条件下，金催化剂可以有效地催化芳烃和末端炔烃的串联组装，以提供有用的炔基化联苯衍生物。
• Copper-Catalyzed 2:1 Coupling Reaction of Arynes with Alkynes
  作者：Hiroto Yoshida、Takami Morishita、Hiromi Nakata、Joji Ohshita

  DOI：10.1021/ol802609j

  日期：2009.1.15

  A formal insertion reaction of two molar amounts of arynes into a C−H bond of terminal alkynes is efficaciously catalyzed by copper(I) chloride, giving 2-alkynylbiaryls in one step.

  氯化铜（I）有效地催化了两个摩尔量的芳烃在末端炔烃的CH键中的正式插入反应，一步即可得到2-炔基联芳基。
• 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.
• FeCl₃ -Mediated Oxidative Spirocyclization of Difluorenylidene Diarylethanes Leading to Dispiro[fluorene-9,5′-indeno[2,1-<i>a</i> ]indene-10′,9′′-fluorene]s
  作者：Jian Zhao、Zhanqiang Xu、Kazuaki Oniwa、Naoki Asao、Yoshinori Yamamoto、Tienan Jin

  DOI：10.1002/anie.201507794

  日期：2016.1.4

  A novel FeCl3‐mediated oxidative spirocyclization for construction of a new class of di‐spirolinked π‐conjugated molecules, dispiro[fluorene‐9,5′‐indeno[2,1‐a]indene‐10′,9′′‐fluorene]s (DSFIIFs), has been reported. The combination of FeCl3 with FeO(OH) triggered an unprecedented double one‐electron oxidation of difluorenylidene diarylethanes to afford the corresponding dispirocycles in high yields

  一种新型的FeCl 3介导的氧化螺环化反应，用于构建新型的双螺链连接的π共轭分子，即双螺[芴-9,5'-茚并[2,1- a ]茚10-10,9'-芴] s（DSFIIFs），已被报道。FeCl 3与FeO（OH）的结合引发了二芴基二芳基乙烷的前所未有的双单电子​​氧化，从而以高收率提供了相应的二螺环。溶液中的最高荧光量子产率高达0.94。该方案也适用于非螺旋连接的二氢茚并茚的合成。