2-(phenylethynyl)-5,4'-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)-5,4'-dimethyl-1,1'-biphenyl
• 英文别名: 4',5-dimethyl-2-(phenylethynyl)-1,1'-biphenyl；5,4'-dimethyl-2-(phenylethynyl)biphenyl；4-Methyl-2-(4-methylphenyl)-1-(2-phenylethynyl)benzene
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: KDOHRDIWGZDEJQ-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)-5,4'-dimethyl-1,1'-biphenyl 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以95%的产率得到2,6-dimethyl-10-phenylphenanthrene
  参考文献：
  名称：

  Cu（II）催化二烯炔的6π-光环化

  摘要：

  二烯的第一个6π-光环化反应得到了发展，它为苯环的合成提供了一个新的有效方法，具有高收率和良好的官能团耐受性。在该转化中，Cu（OTf）2催化剂在炔烃部分转化为烯烃型部分中起关键作用，这意味着二烯炔反应物转化为三烯型底物。因此，该反应通过Cu（II）催化的三烯型衍生物的6π-光环化而进行。

  DOI：

  10.1021/acs.joc.6b02537
• 作为产物：
  描述：

  (E)-1-bromo-2-(phenylethenyl)-5-methylbenzene 在 溴 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 2-(phenylethynyl)-5,4'-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。
• Cu(II)-Catalyzed 6π-Photocyclization of Dienynes
  作者：Ruiwen Jin、Jinjin Chen、Yiyong Chen、Wangsheng Liu、Dawen Xu、Yawei Li、Aishun Ding、Hao Guo

  DOI：10.1021/acs.joc.6b02537

  日期：2016.12.16

  effective protocol for the synthesis of the phenyl ring in excellent yields with nice functional group tolerance. In this transformation, the Cu(OTf)2 catalyst plays a key role in the conversion of alkyne moiety into an alkene-type moiety, which means that the dienyne reactant is converted into a triene-type substrate. Thus, this reaction proceeds via a Cu(II)-catalyzed 6π-photocyclization of triene-type

  二烯的第一个6π-光环化反应得到了发展，它为苯环的合成提供了一个新的有效方法，具有高收率和良好的官能团耐受性。在该转化中，Cu（OTf）2催化剂在炔烃部分转化为烯烃型部分中起关键作用，这意味着二烯炔反应物转化为三烯型底物。因此，该反应通过Cu（II）催化的三烯型衍生物的6π-光环化而进行。
• Selective Electrochemical Synthesis of 9-Aryl-10-sulfonyl Substituted Phenanthrene from Alkynes and Sulfonyl Hydrazides
  作者：Hao-Dong Tian、Zi-Hao Fu、Chen Li、Huang-Chu Lin、Ming Li、Shao-Fei Ni、Li-Rong Wen、Lin-Bao Zhang

  DOI：10.1021/acs.orglett.2c03948

  日期：2022.12.23

  An efficient electrochemical synthesis of sulfonated phenanthrenes via the reaction of internal alkynes with sulfonyl hydrazides has been established. The protocol does not require a metal catalyst or external oxidants, providing a green and mild route to functionalized phenanthrenes. Moreover, the compatibility of various functional groups and decagram-scale experimental conditions demonstrate the

  已经建立了通过内部炔烃与磺酰肼反应的磺化菲的有效电化学合成。该协议不需要金属催化剂或外部氧化剂，为功能化菲提供了一条绿色温和的途径。此外，各种官能团的相容性和十克级实验条件证明了电化学策略的实用性。
• 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.