(Z)-2-benzyl-3-benzylidene-5-chloroisoindolin-1-one | 1127896-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (Z)-2-benzyl-3-benzylidene-5-chloroisoindolin-1-one
• 英文别名: (Z)-2-benzyl-5-chloro-3-(phenylmethylene)isoindolin-1-one；(3Z)-2-benzyl-3-benzylidene-5-chloroisoindol-1-one
• CAS: 1127896-91-6
• 化学式: C₂₂H₁₆ClNO
• 分子量: 345.828
• InChiKey: IHOHNBZEBWGEGX-BKUYFWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-4-氯苯甲酸 在 双(乙腈)氯化钯(II) 、 草酰氯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 (Z)-2-benzyl-3-benzylidene-5-chloroisoindolin-1-one
  参考文献：
  名称：

  Microwave assisted copper-free Sonogashira coupling/5-exo-dig cycloisomerization domino reaction: access to 3-(phenylmethylene)isoindolin-1-ones and related heterocycles

  摘要：

  An efficient microwave assisted one-pot synthesis of substituted 3-(phenylmethylene)isoindolin-1-ones is reported via a copper-free Sonogashira coupling and a regioselective 5-exo-dig cycloisomerization. This domino reaction was also extended to other related heterocycles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.070

文献信息

• Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)2•H2O/DBU under Microwave Irradiation
  作者：Li Zhang、Yongliang Zhang、Xin Wang、Jingkang Shen

  DOI：10.3390/molecules18010654

  日期：——

  Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)2•H2O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy that DBU maybe play a dual role as not only the base, but also as a ligand for copper. The reaction is catalyzed by the complex of Cu(OAc)2•H2O and DBU without other additives.

  介绍了利用 Cu(OAc)2-H2O/DBU 以 2-溴苯甲酰胺和端炔类化合物为原料，通过微波促进高效合成 (Z)-3 亚甲基异吲哚啉-1-酮库。应用各种苯甲酰胺取代基、环取代基（包括杂芳基、芳基乙炔基和脂肪族炔烃）可得到所需的产品，产率从良好到中等，且具有很高的立体选择性。值得注意的是，DBU 可能具有双重作用，它不仅是碱，还是铜的配体。该反应由 Cu(OAc)2-H2O 和 DBU 的络合物催化，无需其他添加剂。
• Assembly of Substituted 3-Methyleneisoindolin-1-ones via a CuI/<scp>l</scp>-Proline-Catalyzed Domino Reaction Process of 2-Bromobenzamides and Terminal Alkynes
  作者：Li Li、Miao Wang、Xiaojing Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol9000922

  日期：2009.3.19

  CuI/L-proline catalyzed coupling of 2-bromobenzamides and terminal alkynes in PrOH (or DMF and DMSO) at 85-110 degrees C and subsequent additive cyclization produces substituted 3-methyleneisoindolin-1-ones. Variation of N-substituents, aromatic ring, and methylene part is possible by using suitable starting materials.
• Microwave assisted copper-free Sonogashira coupling/5-exo-dig cycloisomerization domino reaction: access to 3-(phenylmethylene)isoindolin-1-ones and related heterocycles
  作者：Malik Hellal、Gregory D. Cuny

  DOI：10.1016/j.tetlet.2011.08.070

  日期：2011.10

  An efficient microwave assisted one-pot synthesis of substituted 3-(phenylmethylene)isoindolin-1-ones is reported via a copper-free Sonogashira coupling and a regioselective 5-exo-dig cycloisomerization. This domino reaction was also extended to other related heterocycles. (C) 2011 Elsevier Ltd. All rights reserved.