2-(adamantan-1-yl)isoindolin-1-one

• 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-(adamantan-1-yl)isoindolin-1-one
• 英文别名: 2-(1-Adamantyl)-1-isoindolinone；2-(1-adamantyl)-3H-isoindol-1-one
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: FWXLZNDTOKKKMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  2-(adamantan-1-yl)isoindoline 在 1,4-二氧六环 作用下， 反应 8.0h， 以85%的产率得到2-(adamantan-1-yl)isoindolin-1-one
  参考文献：
  名称：

  异吲哚啉酮的合成：异吲哚啉的选择性二恶烷介导的好氧氧化

  摘要：

  N-烷基和N-芳基-异吲哚啉酮是通过二恶烷介导的异吲哚啉前体的氧化反应制备的。该转化表现出对异茚满碱独特的化学选择性。在氧化过程中手性叔（3°）-苄基位置未消旋，通过后期氧化制备了甲基吲哚洛芬。机理研究表明，选择性的H原子转移可避免许多已知的异吲哚啉酮氧化（副）产物。

  DOI：

  10.1021/acs.joc.8b01920

文献信息

• Divergent Reaction of Isocyanides with <i>o</i>-Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores
  作者：Yi-Ming Zhu、Yizhan Fang、Haiyan Li、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1021/acs.orglett.1c02422

  日期：2021.10.1

  A divergent reaction of isocyanides with o-bromobenzaldehydes for the synthesis of isoindolinone-derived ketenimines and lactams was disclosed. The reaction features readily available reactants, relatively mild conditions, and high yields of products. Ketenimines could be applied in further transformations for access to other functional molecules. A mechanism study showed that the palladium-migration/imine-insertion

  公开了用于合成异吲哚啉酮衍生的烯酮亚胺和内酰胺的异氰化物与邻溴苯甲醛的发散反应。该反应具有反应物易得、条件相对温和、产物收率高等特点。酮亚胺可用于进一步转化以获得其他功能分子。机理研究表明，钯迁移/亚胺插入过程是该反应的关键步骤。
• Thalidomide analogs and methods of use
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：US10730835B2

  公开（公告）日：2020-08-04

  Thalidomide analogs and methods of using the thalidomide analogs are disclosed. Some embodiments of the disclosed compounds exhibit anti-angiogenic and/or anti-inflammatory activity. Certain embodiments of the disclosed compounds are non-teratogenic.

  本研究公开了沙利度胺类似物和使用沙利度胺类似物的方法。所公开化合物的某些实施方案具有抗血管生成和/或抗炎活性。所公开化合物的某些实施方案不致畸。
• Application of Phthalimidine Synthesis with Use of 1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as Dual Synthetic Auxiliaries. 2. Effective Synthesis of Phthalimidines Possessing Bulky Group at 2-Position
  作者：Ichiro Takahashi、Teruki Kawakami、Mako Kimino、Etsushi Hirano、Shigeki Kamimura、Takanori Tamura、Hidehiko Kitajima、Minoru Hatanaka、Hiroyuki Uchida、Akihiko Nomura、Motohiro Tanaka

  DOI：10.3987/com-00-s(i)104

  日期：——

  Potentially bioactive phthalimidines are prepared in fair to good isolated yields by the 1:1 condensation reaction of o-phthalaldehyde with a variety of sterically-hindered primary alkyl amines in the presence of 1,2,3-1 H-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries.
• THALIDOMIDE ANALOGS AND METHODS OF USE
  申请人：The USA, as represented by the Secretary, Department of Health and Human Services

  公开号：US20200325102A1

  公开（公告）日：2020-10-15

  Thalidomide analogs and methods of using the thalidomide analogs are disclosed. Some embodiments of the disclosed compounds exhibit anti-angiogenic and/or anti-inflammatory activity. Certain embodiments of the disclosed compounds are non-teratogenic.
• Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines
  作者：Pawan Thapa、Esai Corral、Sinjinee Sardar、Brad S. Pierce、Frank W. Foss

  DOI：10.1021/acs.joc.8b01920

  日期：2019.1.18

  N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products

  N-烷基和N-芳基-异吲哚啉酮是通过二恶烷介导的异吲哚啉前体的氧化反应制备的。该转化表现出对异茚满碱独特的化学选择性。在氧化过程中手性叔（3°）-苄基位置未消旋，通过后期氧化制备了甲基吲哚洛芬。机理研究表明，选择性的H原子转移可避免许多已知的异吲哚啉酮氧化（副）产物。