2-(2'-hydroxy-2'-methylpropynyl)-N-p-tolyl benzamide | 293744-68-0

• 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-(2'-hydroxy-2'-methylpropynyl)-N-p-tolyl benzamide
• CAS: 293744-68-0
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: KNEAFWQQZDVAQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2'-hydroxy-2'-methylpropynyl)-N-p-tolyl benzamide 在 palladium on activated charcoal 氢气 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 3-(2'-hydroxy-2'-methylpropyl)-N-p-tolyl isoindolin-1-one
  参考文献：
  名称：

  Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones

  摘要：

  A highly regio- and stereoselective method for the synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)(2)PdCl2, CuI, and Et3N in DMF mostly at 80 degrees C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00359-8
• 作为产物：
  描述：

  2-碘苯甲酸 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 五氯化磷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.0h， 生成 2-(2'-hydroxy-2'-methylpropynyl)-N-p-tolyl benzamide
  参考文献：
  名称：

  Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones

  摘要：

  A highly regio- and stereoselective method for the synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)(2)PdCl2, CuI, and Et3N in DMF mostly at 80 degrees C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00359-8

文献信息

• A Highly Regio and Stereoselective Synthesis of (<i>Z</i>)-3-Aryl(alkyl)idene Isoindolin-1-ones via Palladium Catalyzed Annulation of Terminal Alkynes
  作者：M. Khan、Nitya Kundu

  DOI：10.1055/s-1997-1049

  日期：——

  o-Iodobenzamide or its N-substituted derivatives 4-10 and terminal alkynes 11-17 reacted in DMF in the presence of bis(triphenylphosphine)palladium(II)chloride, cuprous iodide and triethylamine leading to (Z)-3-arylidene isoindolin-1-ones (22, 24, 27 and 28) or o-alkynyl N-substituted benzamides (I). The latter could be cyclised with sodium in ethanol in a completely regio and stereoselective manner to (Z)-3-aryl(alkyl)idene isoindolin-1-ones 18-35.

  o-碘苯甲酰胺或其N-取代衍生物4-10与末端炔烃11-17在二甲基甲酰胺中，在双(三苯基膦)二氯化钯、碘化亚铜和三乙胺的存在下反应，得到（Z）-3-芳基亚甲基异吲哚啉-1-酮（22, 24, 27 和 28）或o-炔基N-取代苯甲酰胺（I）。后者可在乙醇中与钠完全区域和立体选择性环化为（Z）-3-芳基（烷基）亚甲基异吲哚啉-1-酮18-35。
• Two (<i>Z</i>)-3-aryl(alkyl)ideneisoindolin-1-ones
  作者：N. G. Kundu、M. W. Khan、S. Guha、A. K. Mukherjee

  DOI：10.1107/s0108270198009962

  日期：1999.2.15

  Two isoindolin-1-one derivatives, (Z)-3-(p-methoxybenzylidene)isoindolin-1-one [C16H13NO2, (2)] and (Z)-3-(2-hydroxy-2-methylpropylidene)-N-(p-tolyl)isoindolin-1-one [C19H19NO2, (3)], were synthesized by palladium-catalyzed hetero-annulation. The molecules of both compounds, which have a Z configuration, contain two planar parts, namely, the isoindolinone moiety and the phenyl ring. The r.m.s. deviation (0.111 Angstrom) from the least-squares plane through the non-H atoms in compound (2) illustrates the overall molecular planarity. In (3), the phenyl ring is twisted out of the isoindolinone plane by 79.8(1)degrees. Intermolecular hydrogen bonds link the molecules in (2) and (3) into infinite one-dimensional chains.