2-(4-bromophenyl)isoindoline

• 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: 2-(4-bromophenyl)isoindoline
• 英文别名: 2-(4-Bromophenyl)-1,3-dihydroisoindole
• 化学式: C₁₄H₁₂BrN
• 分子量: 274.16
• InChiKey: AOTLWDQSZSDCEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)isoindoline 在 亚硝酸特丁酯 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(4-bromophenyl)-3-hydroxyisoindolin-1-one
  参考文献：
  名称：

  叔丁基亚硝酸盐（TBN）引发的自由基sp3 C–H活化继电器（CHAR）实现的异吲哚啉的氧化脱敏

  摘要：

  TBN引发的自由基sp 3 C–H活化继电器（CHAR）实现了异吲哚啉的氧化脱对称，从而以高收率提供了一系列ω-羟基内酰胺。该反应表现出广泛的底物范围和官能团耐受性，甚至N-烷基异二氢吲哚也可以被很好地耐受。机理研究表明，C–H键氧化，双氧捕集和分子内1,5-H移位可能是实现氧化脱对称的关键步骤。

  DOI：

  10.1055/s-0040-1706010
• 作为产物：
  描述：

  邻二氯苄 、 4-溴苯胺 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.33h， 以98%的产率得到2-(4-bromophenyl)isoindoline
  参考文献：
  名称：

  Scale-Up of the Green Synthesis of Azacycloalkanes and Isoindolines under Microwave Irradiation

  摘要：

  A green approach to N-heterocyclization reactions ranging in scale from 20 mmol to 1 mol performed under microwave irradiation in open vessels has been investigated. By using water as the solvent and no transition metal catalysts, N-heterocycles are formed in a fraction of the time needed for conventional synthesis of these compounds. The obtained yields indicate that reactions can be performed at atmospheric pressure using the same reaction conditions as the corresponding sealed-vessel reactions. Single-mode and multimode microwave cavities have been used for open-vessel synthesis without changing reaction times producing similar yields.

  DOI：

  10.1021/op0601722

文献信息

• Iron‐Catalysed Switchable Synthesis of Pyrrolidines <i>vs</i> Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives <i>via</i> Hydrosilylation
  作者：Duo Wei、Chakkrit Netkaew、Christophe Darcel

  DOI：10.1002/adsc.201801656

  日期：2019.4.16

  A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines

  本文提出了通过切换铁络合物催化剂通过乙酰丙酸和乙酰丙酸酯的氢化硅烷化选择性生产吡咯烷对吡咯烷酮。该反应在可见光照射和热条件下用各种苯胺和烷基胺有效地进行，其中43个实例的分离产率高达93％。值得注意的是，在相似的条件下，通过苯胺分别与1,5-或1,6-酮酸反应，可以高效合成环状胺（如哌啶和氮杂环庚烷），产率高达92％。同样，可以从2-甲酰基苯甲酸以57-93％的收率制备N- arylinsolidoline化合物。
• Visible-Light Induced Isoindoles Formation To Trigger Intermolecular Diels–Alder Reactions in the Presence of Air
  作者：Chao Lin、Le Zhen、Yong Cheng、Hong-Jin Du、Hui Zhao、Xiaoan Wen、Ling-Yi Kong、Qing-Long Xu、Hongbin Sun

  DOI：10.1021/acs.orglett.5b01078

  日期：2015.6.5

  Visible-light induced isoindole formation triggered an intermolecular Diels-Alder reaction with dienophiles such as acetylenedicarboxylate and maleimides in the presence of air. The reaction resulted in excellent diastereoselctivity and high yields under mild reaction conditions. This protocol provides an atom-economical, transition-metal-free (TM-free) and straightforward approach to structurally diverse bridged-ring heterocycles from easily accessible molecules.
• Oxidative Desymmetrization of Isoindolines Realized by tert-Butyl Nitrite (TBN) Initiated Radical sp3 C–H Activation Relay (CHAR)
  作者：Yu Yuan、Xiaodong Jia、Zheng Sun、Yu Shao、Shuwei Zhang、Yuxian Zhang

  DOI：10.1055/s-0040-1706010

  日期：2021.5

  An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp3 C–H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N-alkyl iso­indolines can be well tolerated. The mechanistic study shows that the C–H bond oxidation, dioxygen trapping and intramolecular 1,5-H

  TBN引发的自由基sp 3 C–H活化继电器（CHAR）实现了异吲哚啉的氧化脱对称，从而以高收率提供了一系列ω-羟基内酰胺。该反应表现出广泛的底物范围和官能团耐受性，甚至N-烷基异二氢吲哚也可以被很好地耐受。机理研究表明，C–H键氧化，双氧捕集和分子内1,5-H移位可能是实现氧化脱对称的关键步骤。
• Scale-Up of the Green Synthesis of Azacycloalkanes and Isoindolines under Microwave Irradiation
  作者：T. Michael Barnard、Grace S. Vanier、Michael J. Collins

  DOI：10.1021/op0601722

  日期：2006.11.1

  A green approach to N-heterocyclization reactions ranging in scale from 20 mmol to 1 mol performed under microwave irradiation in open vessels has been investigated. By using water as the solvent and no transition metal catalysts, N-heterocycles are formed in a fraction of the time needed for conventional synthesis of these compounds. The obtained yields indicate that reactions can be performed at atmospheric pressure using the same reaction conditions as the corresponding sealed-vessel reactions. Single-mode and multimode microwave cavities have been used for open-vessel synthesis without changing reaction times producing similar yields.