2-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline | 1415989-71-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline
• 英文别名: 2-[2-(2-chlorophenyl)ethynyl]-N,N-dimethylaniline
• CAS: 1415989-71-7
• 化学式: C₁₆H₁₄ClN
• 分子量: 255.747
• InChiKey: NYPONEPEYNFSON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline 在 叔丁基过氧化氢 、 copper(l) iodide 、 lithium chloride 、 palladium(II) bromide 作用下， 以 癸烷 、 甲苯 为溶剂， 以40%的产率得到(2-chlorophenyl)(1-methyl-1H-indol-3-yl)methanone
  参考文献：
  名称：

  钯-铜-共催化的分子内氧化偶联：合成3-acylindoles的有效和原子经济的策略。

  摘要：

  展示了一种新的高效催化方法，可在Pd-Cu共催化的氧化条件下合成3-acylindoles。叔丁基氢过氧化物（TBHP）在该方法中不仅充当氧化剂，而且充当氧气源。该方法允许从容易获得的原料中快速且原子经济地组装3-acylindoles，并能耐受各种官能团。

  DOI：

  10.1039/c2cc37805a
• 作为产物：
  描述：

  2-氯苯乙炔 、 邻碘-N,N-二甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline
  参考文献：
  名称：

  Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles

  摘要：

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.

  DOI：

  10.1021/jo301741j

文献信息

• Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
  作者：Xiao-Feng Xia、Ning Wang、Lu−Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo301741j

  日期：2012.10.19

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.
• Palladium–copper-cocatalyzed intramolecular oxidative coupling: an efficient and atom-economical strategy for the synthesis of 3-acylindoles
  作者：Xiao-Feng Xia、Lu-Lu Zhang、Xian-Rong Song、Yan-Ning Niu、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1039/c2cc37805a

  日期：——

  A new and efficient catalytic approach to the synthesis of 3-acylindoles under Pd-Cu-cocatalyzed oxidative conditions is demonstrated. tert-Butyl hydroperoxide (TBHP) acts not only as the oxidant, but also as an oxygen source in the approach. The process allows quick and atom-economical assembly of 3-acylindoles from readily available starting materials and tolerates a broad range of functional groups

  展示了一种新的高效催化方法，可在Pd-Cu共催化的氧化条件下合成3-acylindoles。叔丁基氢过氧化物（TBHP）在该方法中不仅充当氧化剂，而且充当氧气源。该方法允许从容易获得的原料中快速且原子经济地组装3-acylindoles，并能耐受各种官能团。