2-(4-(phenylethynyl)phenyl)acetonitrile | 54737-74-5

• 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-(4-(phenylethynyl)phenyl)acetonitrile
• 英文别名: 2-(4-(2-phenylethynyl)phenyl)acetonitrile；[4-(phenylethinyl)phenyl]acetonitrile；4-(phenylethynyl)phenylacetonitrile；4-phenylethynyl-benzylnitrile；[4-(Phenylethinyl)phenyl]-acetonitrile；2-[4-(2-phenylethynyl)phenyl]acetonitrile
• CAS: 54737-74-5
• 化学式: C₁₆H₁₁N
• 分子量: 217.27
• InChiKey: AURCBNQFRGIETD-UHFFFAOYSA-N

物化性质

• 沸点：
  392.1±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-(phenylethynyl)phenyl)acetonitrile 在 氢氧化钾 、 sodium hydroxide 、 双氧水 作用下， 生成 N-Benzyloxycarbonyl-1-<4-(phenylethinyl)-phenyl>-cyclopropylamin
  参考文献：
  名称：

  Antiarrhythmic agents. 2-, 3-, and 4-Substituted benzylamines

  摘要：

  The synthesis of a series of 2-, 3-, and 4-substituted benzylamine derivatives is described. These compounds were studied for their effect on experimental cardiac arrhythmias. Many of the derivatives, but in particular 2-(p-methoxyphenylethynyl)benzylamine (3d), alpha,alpha-dimethyl-4y(phenylethynyl)benzylamine (7a), and alpha,alpha-dimethyl-4-phenethylbenzylamine (12g), showed good antiarrhythmic activity.

  DOI：

  10.1021/jm00236a006
• 作为产物：
  描述：

  [4-(2-苯基乙炔基)苯基]甲醇 在 氯化亚砜 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(4-(phenylethynyl)phenyl)acetonitrile
  参考文献：
  名称：

  Antiarrhythmic agents. 2-, 3-, and 4-Substituted benzylamines

  摘要：

  The synthesis of a series of 2-, 3-, and 4-substituted benzylamine derivatives is described. These compounds were studied for their effect on experimental cardiac arrhythmias. Many of the derivatives, but in particular 2-(p-methoxyphenylethynyl)benzylamine (3d), alpha,alpha-dimethyl-4y(phenylethynyl)benzylamine (7a), and alpha,alpha-dimethyl-4-phenethylbenzylamine (12g), showed good antiarrhythmic activity.

  DOI：

  10.1021/jm00236a006

文献信息

• Selective α‐Monomethylation by an Amine‐Borane/ <i>N</i> , <i>N</i> ‐Dimethylformamide System as the Methyl Source
  作者：Hui‐Min Xia、Feng‐Lian Zhang、Tian Ye、Yi‐Feng Wang

  DOI：10.1002/anie.201804794

  日期：2018.9.3

  A new and practical α‐monomethylation strategy using an amine‐borane/N,N‐dimethylformamide (R3N‐BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α‐monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N‐BH3 donated

  开发了一种新的实用的α-单甲基化策略，该方法使用胺-硼烷/ N，N-二甲基甲酰胺（R 3 N-BH 3 / DMF）系统作为甲基来源。已发现该方案对芳基乙腈和芳基乙酰胺的α-单甲基化有效。机理研究表明，DMF的甲酰基传递了碳原子和甲基的一个氢原子，而R 3 N-BH 3则贡献了其余的两个氢原子。如此独特的反应路径使得使用Me 2 NH-BH 3 / d可控制地组装CDH 2，CD 2 H和CD 3单元。7 ‐ DMF ，Me 3 N‐BD 3 / DMF和Me 3 N‐BD 3 / d 7 ‐ DMF系统。证实了该方法在抗炎药氟比洛芬及其各种氘标记衍生物的简便合成中的进一步应用。
• Efficient copper-free Sonogashira coupling of aryl chlorides with palladium on charcoal
  作者：Anna Komáromi、Zoltán Novák

  DOI：10.1039/b810928a

  日期：——

  Palladium on charcoal serves as an efficient and reusable solid supported catalyst for the Sonogashira coupling of aryl chlorides with terminal acetylenes in the presence of a bulky, electron-rich biphenyl type ligand (XPhos), without copper co-catalyst.

  活性炭负载钯作为高效且可重复使用的固载催化剂，在无铜共催化剂存在下，通过体积庞大、电子丰富的联苯型配体（XPhos）促进芳基氯与末端炔烃的Sonogashira偶联反应。
• Ligand-free (<i>Z</i>)-selective transfer semihydrogenation of alkynes catalyzed by <i>in situ</i> generated oxidizable copper nanoparticles
  作者：Rafał Kusy、Karol Grela

  DOI：10.1039/d1gc01206a

  日期：——

  of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation

  在此，我们提出了在氢供体（如氨硼烷和绿色质子溶剂）存在下，基于原位生成的 CuNPs的炔烃的( Z ) 选择性转移半氢化。这种环保方法的特点是操作简单，同时具有高立体选择性和化学选择性以及官能团兼容性。CuNPs在半氢化反应完成后自动氧化形成水溶性氨络合物，因此催化剂可以通过简单的相分离多次重复使用，无需任何特殊的再生过程。形成NH 4 B(OR) 4可以很容易地转化回氨硼烷或硼酸。此外，还提出了涉及 Suzuki 反应和半氢化的一锅串联序列，这可以最大限度地减少化学废物的产生。
• Substituted-cyano-2-[4-(phenyl-ethynyl)phenyl]-1-1
  申请人：Sandoz Ltd.

  公开号：US05219876A1

  公开（公告）日：1993-06-15

  The invention provides compounds of formula I wherein R, R.sub.1 and Az are as defined in the description, the fungicidal use of such compounds, compositions for facilitating such use and the preparation of compounds of formula I.

  本发明提供了公式I的化合物，其中R、R.sub.1和Az如描述中所定义，这些化合物的杀真菌用途，促进此类用途的组合物以及公式I化合物的制备。
• 10.1002/ejoc.202400405
  作者：Hong, Yuwei、Qin, Yizhou、Yang, Xiong、Zhou, Lanxi、Yuan, Yao、Zhu, Gangguo

  DOI：10.1002/ejoc.202400405

  日期：——

  producing a library of functionalized trifluoromethylated δ,ϵ- or γ,δ-unsaturated aldehydes in moderate to excellent yields with good functional group tolerance. The controllable installation of three functional groups, such as CF3, CHO, and a C−C double bond, provides a very attractive protocol for rapid synthesis of complex molecules from simple starting materials.

  实现了可见光光催化甲酰基迁移触发的远程去饱和，以中等至优异的收率和良好的官能团耐受性产生官能化三氟甲基化δ,ε-或γ,δ-不饱和醛库。三个官能团的可控安装，例如 CF 3 、CHO 和 C−C 双键，为从简单起始材料快速合成复杂分子提供了非常有吸引力的方案。