5,6-dimethoxy-2-phenylisoindoline-1,3-dione | 55315-86-1

• 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: 5,6-dimethoxy-2-phenylisoindoline-1,3-dione
• 英文别名: 5,6-Dimethoxy-2-phenylisoindole-1,3-dione
• CAS: 55315-86-1
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: NRAIYKDPUZECTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  468.9±55.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸 在 bis(triphenylphosphine)palladium(II)-chloride 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 氘代氯仿 、 N,N-二甲基乙酰胺 为溶剂， 115.0 ℃ 、655.0 kPa 条件下， 反应 1.2h， 生成 5,6-dimethoxy-2-phenylisoindoline-1,3-dione
  参考文献：
  名称：

  Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines

  摘要：

  A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the desired products. Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction. The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.

  DOI：

  10.1021/jo00023a023

文献信息

• Cuprous Oxide Catalyzed Oxidative CC Bond Cleavage for CN Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
  作者：Min Wang、Jianmin Lu、Jiping Ma、Zhe Zhang、Feng Wang

  DOI：10.1002/anie.201508071

  日期：2015.11.16

  cleavage of a CC bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative CC bond cleavage of ketone for CN bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In‐depth studies show that both α‐CH and β‐CH bonds adjacent

  CC键的选择性氧化裂解为有机骨架的功能化提供了直接的方法。本文报道的是氧化Ç  C键酮对C裂解 N键形成在与分子氧作为氧化剂的氧化亚铜催化剂。大量的酮和胺以中等到极好的收率被转化为环状酰亚胺。深入的研究表明，与羰基相邻的α- CH和β- CH键对于CC键的裂解都是必不可少的。DFT计算表明该反应是由α- CH键的氧化引发的。胺降低C的活化能C键裂解，从而促进反应。提出了对C insightC键断裂机理的新见解。
• Ruthenium(II)‐Catalyzed CH Activation with Isocyanates: A Versatile Route to Phthalimides
  作者：Suman De Sarkar、Lutz Ackermann

  DOI：10.1002/chem.201404261

  日期：2014.10.20

  A cationic ruthenium(II)‐complex was utilized in the efficient synthesis of phthalimide derivatives by CH activation with synthetically useful amides. The reaction proceeded through a mechanistically unique insertion of a cycloruthenated species into a CHet multiple bond of isocyanate. The novel method also proved applicable for the synthesis of heteroaromatic unsymmetric diamides as well as a potent

  阳离子钌（II）络合物用于通过CH与合成有用的酰胺活化而有效合成邻苯二甲酰亚胺衍生物。该反应通过一个cycloruthenated物种的机理上独特插入一个C进行异氰酸酯的Het多重键。该新方法还证明可用于杂芳族不对称二酰胺以及强效COX-2酶抑制剂的合成。
• US3987174A
  申请人：——

  公开号：US3987174A

  公开（公告）日：1976-10-19
• US4054654A
  申请人：——

  公开号：US4054654A

  公开（公告）日：1977-10-18
• Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines
  作者：Robert J. Perry、S. Richard Turner

  DOI：10.1021/jo00023a023

  日期：1991.11

  A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the desired products. Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction. The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.