(Z)-3-(4-chlorobenzylidene)-2,3-dihydro-1H-isoindolin-1-one | 1049694-20-3

• 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-chlorobenzylidene)-2,3-dihydro-1H-isoindolin-1-one
• 英文别名: (Z)-3-(4-chlorobenzylidene)isoindolin-1-one；(3Z)-3-[(4-chlorophenyl)methylidene]isoindol-1-one
• CAS: 1049694-20-3
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: RIXZLNQJMXPBQG-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘苯甲酸 、 对氯苯丙炔酸 在 copper(l) iodide 、 ammonium acetate 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以69%的产率得到(Z)-3-(4-chlorobenzylidene)-2,3-dihydro-1H-isoindolin-1-one
  参考文献：
  名称：

  铜催化的2-卤代苯甲酸，炔基羧酸和乙酸铵三组分偶联选择性合成异吲哚啉-1-酮和异喹啉-1-酮

  摘要：

  AbstractIsoindolin‐1‐ones and isoquinolin‐1‐ones were selectively synthesized from the reaction of 2‐halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one‐pot conditions provided isoindolin‐1‐ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin‐1‐ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin‐1‐ones and isoquinolin‐1‐ones in good yields.magnified image

  DOI：

  10.1002/adsc.201400451

文献信息

• High stereoselectivity synthesis of <i>Z</i>-3-methyleneisoindolin-1-ones on a Cu/ETS-10 catalyst <i>via</i> domino coupling–cyclization without the use of protective groups and ligands
  作者：Huiling Hu、Changjun Liu、Chaojie Zhu、Chenghong Liu、Tiandi Tang

  DOI：10.1039/d3nj04522f

  日期：——

  product synthesis. Herein, we report a novel strategy that uses basic ETS-10 zeolite-supported copper (Cu/ETS-10) as a catalyst for the highly selective synthesis of Z-3-methyleneisoindolin-1-ones in the absence of ligands. It was found that the rigidity of the zeolite skeleton was conducive to the high configurational selectivity of the product. The Cu/ETS-10 catalyst was easily recovered by simple filtration

  控制二分子反应中偶联位点的空间选择性对于立体选择性产物合成至关重要。在此，我们报告了一种新策略，使用碱性 ETS-10 沸石负载的铜 (Cu/ETS-10) 作为催化剂，在没有配体的情况下高选择性合成Z -3-亚甲基异吲哚啉-1-酮。研究发现，沸石骨架的刚性有利于产物的高构型选择性。Cu/ETS-10催化剂通过简单过滤即可轻松回收，并且可以重复使用五次而不会损失其初始活性。
• A Tandem Elimination−Cyclization−Suzuki Approach: Efficient One-Pot Synthesis of Functionalized (<i>Z</i>)-3-(Arylmethylene)isoindolin-1-ones
  作者：Caiyun Sun、Bin Xu

  DOI：10.1021/jo801219j

  日期：2008.9.19

  A novel and efficient one-pot regioselective elimination-cyclization-Suzuki approach was developed to afford (Z)-3-arylmethyleneisoindolin-1-ones in good to excellent yields from easily accessible o-gem-dihalovinylbenzamides and organoboron reagents.
• Copper-Catalyzed Selective Synthesis of Isoindolin-1-ones and Isoquinolin-1-ones from the Three-Component Coupling of 2-Halobenzoic Acid, Alkynylcarboxylic Acid and Ammonium Acetate
  作者：Francis Mariaraj Irudayanathan、Jieun Noh、Jinseop Choi、Sunwoo Lee

  DOI：10.1002/adsc.201400451

  日期：2014.11.3

  AbstractIsoindolin‐1‐ones and isoquinolin‐1‐ones were selectively synthesized from the reaction of 2‐halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one‐pot conditions provided isoindolin‐1‐ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin‐1‐ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin‐1‐ones and isoquinolin‐1‐ones in good yields.magnified image