(Z)-3-(4-methoxyphenyl)methylidene-N-phenyl-isoindolin-1-one | 1415662-25-7

• 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)-3-(4-methoxyphenyl)methylidene-N-phenyl-isoindolin-1-one
• 英文别名: (Z)-3-(4-methoxybenzylidene)-2-phenylisoindolin-1-one；(3Z)-3-[(4-methoxyphenyl)methylidene]-2-phenylisoindol-1-one
• CAS: 1415662-25-7
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: NDUHOMZQLQSZCZ-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  麦锈灵 、 4-乙炔基苯甲醚 在 双(乙腈)氯化钯(II) 、 水 、 十六烷基三甲基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 异烟醛 (4-吡啶亚甲基)腙 作用下， 反应 1.0h， 以90%的产率得到(Z)-3-(4-methoxyphenyl)methylidene-N-phenyl-isoindolin-1-one
  参考文献：
  名称：

  A novel approach for highly regio- and stereoselective synthesis of (Z)-3-methyleneisoindoline-1-ones in aqueous micellar medium

  摘要：

  An environmentally benign and operationally simple methodology was developed for the regio- and stereoselective synthesis of (Z)-3-methyleneisoindolinones in aqueous micellar medium from 2-iodo-N-phenyl-benzamides and terminal alkyne by Cu-free domino Sonogashira reaction followed by 5-exo-dig-cyclization using Pd(CH3CN)Cl-2 as catalyst and 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene as ligand under aerobic condition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.001

文献信息

• A novel approach for highly regio- and stereoselective synthesis of (Z)-3-methyleneisoindoline-1-ones in aqueous micellar medium
  作者：Swarbhanu Sarkar、Samrat Dutta、Rajdip Dey、Subhendu Naskar

  DOI：10.1016/j.tetlet.2012.10.001

  日期：2012.12

  An environmentally benign and operationally simple methodology was developed for the regio- and stereoselective synthesis of (Z)-3-methyleneisoindolinones in aqueous micellar medium from 2-iodo-N-phenyl-benzamides and terminal alkyne by Cu-free domino Sonogashira reaction followed by 5-exo-dig-cyclization using Pd(CH3CN)Cl-2 as catalyst and 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene as ligand under aerobic condition. (C) 2012 Elsevier Ltd. All rights reserved.
• A green approach for the regio- and stereo-selective syntheses of (Z)-3-methyleneisoindoline-1-ones in aqueous medium
  作者：Nivedita Chatterjee、Swarbhanu Sarkar、Rammyani Pal、Asish Kumar Sen

  DOI：10.1016/j.tetlet.2013.05.004

  日期：2013.7

  A high yielding novel methodology was developed for the regio- and stereo-selective syntheses of (Z)-3-methyleneisoindoline-1-ones from substituted 2-phenylethynyl benzamides, generated in situ from 2(phenylcarbamoyl)phenyl-1-H-imidazole-1-sulfonates and corresponding alkyne by Cu-free Sonogashira cross-coupling-5-exo-dig-cyclization in aqueous medium under sonication. The compound could easily be purified by recrystallization from EtOAc without column chromatography. (C) 2013 Elsevier Ltd. All rights reserved.
• Copper(II)-Catalyzed Tandem Synthesis of Substituted 3-Methyleneisoindolin-1-ones
  作者：Jie Pan、Zhen Xu、Runsheng Zeng、Jianping Zou

  DOI：10.1002/cjoc.201300346

  日期：2013.8

  AbstractAn efficient strategy for the synthesis of a variety of 3‐methyleneisoindolin‐1‐ones has been developed. The reaction proceeded from coupling of 2‐iodobenzamides (or 2‐bromobenzamides) and terminal alkynes via Cu(OAc)2·H2O/2,2′‐biimidazole catalyzed in DMF at 60°C and subsequent additive cyclization produced substituted 3‐methyleneisoindolin‐1‐ones in good to excellent yields.