5-chloro-2-phenylisoindolin-1-one | 1594103-36-2

• 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: 5-chloro-2-phenylisoindolin-1-one
• 英文别名: 5-chloro-2-phenyl-3H-isoindol-1-one
• CAS: 1594103-36-2
• 化学式: C₁₄H₁₀ClNO
• 分子量: 243.692
• InChiKey: ZPPYGNHELTZIOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  C₁₃H₉BrClN 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 1,2-双[(2R,5R)-2,5-二乙基磷杂环戊烷基]苯(1,5-环辛二烯)铑(I)四氟硼酸盐 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 5-chloro-2-phenylisoindolin-1-one
  参考文献：
  名称：

  Direct Access to Benzolactams and Benzolactones via Nickel Catalyzed Carbonylation with CO2

  摘要：

  A new nickel catalyzed cross‐electrophile coupling for accessing γ‐lactams (isoindolinones) as well as γ‐lactones (isobenzofuranones) via carbonylation with CO2 is documented. The protocol exploits the synergistic role of redox‐active Ni(II) complexes and AlCl3 as a CO2 activator/oxygen scavenger, leading to the formation of a wide range of cyclic amides and esters (28 examples) in good to high yields (up to 87%). A dedicated computational investigation revealed the multiple roles played by AlCl3. In particular, the simultaneous transient protection of the pendant amino group of the starting reagents and the formation of the electrophilically activated CO2‐AlCl3 adduct are shown to concur in paving the way for an energetically favorable mechanistic pathway.

  DOI：

  10.1002/chem.202401658

文献信息

• Metal-Free Cascade Formation of Intermolecular C–N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction
  作者：Zirong Zou、Genuo Cai、Weihao Chen、Canlin Zou、Yamei Li、Hongting Wu、Lu Chen、Jinhui Hu、Yibiao Li、Yubing Huang

  DOI：10.1021/acs.joc.1c01845

  日期：2021.11.5

  An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C–N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment

  已经实现了通过 2-羧基苯甲醛和胺的还原/酰胺化来构建取代异吲哚啉酮的电化学方案。在无金属和无外部还原剂的电解条件下，该反应实现了分子间 C-N 键的级联形成，并以中等至良好的产率提供了一系列异吲哚啉酮。氘标记实验证明，产物亚甲基中的氢主要由体系中的H 2 O提供。
• Synthesis of isoindolinones via inverse-electron demand Diels–Alder cycloadditions
  作者：Raymond J. Huntley、Mahender Gurram、Joel R. Walker、David M. Jenkins、Emmanuel J. Robé、Feryan Ahmed

  DOI：10.1016/j.tetlet.2014.02.093

  日期：2014.4

  A new synthetic method has been developed for the synthesis of 2,4,5-substituted isoindolinones by means of intramolecular inverse-electron demand Diels-Alder cycloaddition reactions of substituted pyridazines. By taking advantage of the inherent reactivity of an intermediate chloropyridazine, a diverse set of analogues were prepared from common reagents and intermediates. (C) 2014 Elsevier Ltd. All rights reserved.