1,3-dimethyl-2-(phenylethynyl)-1H-indole | 1235885-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3-dimethyl-2-(phenylethynyl)-1H-indole
• 英文别名: 1,3-Dimethyl-2-(2-phenylethynyl)indole；1,3-dimethyl-2-(2-phenylethynyl)indole
• CAS: 1235885-95-6
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: QMTSQZHIWXJYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 sodium acetate 、 palladium diacetate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 13.0h， 生成 1,3-dimethyl-2-(phenylethynyl)-1H-indole
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Alkynylation of Pyrroles and Azoles under Mild Conditions: Application to the Synthesis of a Dopamine D-4 Receptor Agonist

  摘要：

  A mild and general method for the direct alkynylation of azoles such as pyrrole, indole, and 7-azaindole is described here. Using a simple catalytic system such as Pd(OAc)(2) (2.5 mol %), P(tBu)(2)Me center dot HBF4 (5 mol %), and NaOAc (2 equiv) allowed the regioselective introduction of various alkynyl residues at the C-2 position of pyrroles. Interestingly, C-2 alkynylation was also observed on C-3-substituted indoles, whereas classical C-3 alkynylation was obtained on selected unsubstituted indoles and 7-azaindole. Our methodology has been illustrated by the efficient synthesis of a potential schizophrenia drug (dopamine D-4 inhibitor).

  DOI：

  10.1021/acs.joc.5b01093

文献信息

• Palladium-catalyzed direct oxidative Heck–Cassar–Sonogashira type alkynylation of indoles with alkynes under oxygen
  作者：Luo Yang、Liang Zhao、Chao-Jun Li

  DOI：10.1039/c0cc00014k

  日期：——

  A novel Pd(II) catalyzed direct oxidative Heck-Cassar-Sonogashira type alkynylation of indoles with terminal alkynes under an atmosphere of O(2) is developed. Unlike previous methods, the reaction does not require the pregeneration of indolyl halide or alkynyl halide. Furthermore, only a catalytic amount of base is required and oxygen was used as the ultimate "green" terminal oxidant.

  开发了一种新型的Pd（II）在O（2）气氛下催化直接氧化Heck-Cassar-Sonogashira型吲哚与末端炔烃的炔基化反应。与以前的方法不同，该反应不需要吲哚基卤或炔基卤的预生成。此外，仅需要催化量的碱，并且氧气被用作最终的“绿色”末端氧化剂。