methyl 3-oxoisoindoline-1-carboxylate | 1198391-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-oxoisoindoline-1-carboxylate
• 英文别名: methyl isoindolin-1-one-3-carboxylate；methyl 3-oxo-2,3-dihydro-1H-isoindole-1-carboxylate；methyl 3-oxo-1,2-dihydroisoindole-1-carboxylate
• CAS: 1198391-70-6
• 化学式: C₁₀H₉NO₃
• mdl: MFCD18417620
• 分子量: 191.186
• InChiKey: FTFQEIGJZWIFPE-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-oxoisoindoline-1-carboxylate 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 作用下， 70.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以92%的产率得到rac-methyl (3S,3aR,7aS)-octahydroisoindol-1-one-3-carboxylate
  参考文献：
  名称：

  Efficient access to (1H)-isoindolin-1-one-3-carboxylic acid derivatives by orthopalladation and carbonylation of methyl arylglycinate substrates

  摘要：

  The orthopalladation of methyl arylglycinate derivatives has been studied. The reaction proceeds efficiently for different electron-withdrawing and electron-releasing substituents at the aryl ring. The carbonylation of the orthopalladated complexes affords, in a single step, substituted (1H)-isoindolin-1-one-3-carboxylates. These compounds constitute valuable synthetic intermediates and can be transformed diastereoselectively into octahydroisoindole-1-carboxylic acid derivatives, an important scaffold in the synthesis of many biologically active compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.064
• 作为产物：
  描述：

  methyl 2-(4-methoxyphenyl)-3-oxoisoindoline-1-carboxylate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以77%的产率得到methyl 3-oxoisoindoline-1-carboxylate
  参考文献：
  名称：

  通过路易斯酸催化的多米诺Strecker内酰胺化/烷基化方法制备异吲哚啉酮，异喹啉酮和THIQ

  摘要：

  据报道，一锅，三组分合成的广泛取代的异吲哚啉酮和异喹啉酮具有路易斯酸催化的有效斯特雷克反应和内酰胺化顺序，可提供高至高收率的产物。该方法还扩展到高产率合成四氢异喹啉（THIQs）。

  DOI：

  10.1021/acs.orglett.5b03331

文献信息

• 一种色满桥环异吲哚酮及其制备方法
  申请人：河南大学

  公开号：CN108948034B

  公开（公告）日：2019-09-13

  本发明公开了一种色满桥环异吲哚酮及其制备方法，属于有机合成技术领域。本发明通过将异吲哚酮和邻羟基查尔酮加在乙腈溶剂中，以对甲苯磺酸为催化剂，在35 oC的温度下发生Michael加成/缩合/环化串联反应来制备色满桥环异吲哚酮。本发明避免分离中间体，反应完全后，通过过滤或柱色谱即可拿到纯品。本发明具有反应条件温和、操作简单、底物范围广等优点。
• A Brønsted Acid‐Catalyzed Michael Addition/Cyclization Sequence for the Diastereoselective Assembly of Chroman‐Bridged Polycyclic Isoindolinones
  作者：Shaojing Jin、Jia Guo、Dongmei Fang、Yongwei Huang、Qilin Wang、Zhanwei Bu

  DOI：10.1002/adsc.201801227

  日期：2019.2

  The first p‐TSA‐catalyzed highly diastereoselective Michael addition/cyclization of 3‐carboxylate‐substituted isoindolinones and ortho‐hydroxychalcones was developed to access a wide range of chroman‐bridged polycyclic isoindolinones. This reaction represents a novel and efficient method for the construction of complex bridged polycyclic isoindolinones. Moreover, several derivatizations were carried

  开发了第一个由p ‐TSA催化的3-羧酸酯取代的异吲哚啉酮和邻羟基查尔酮的非对映选择性高迈克尔加成/环化反应，可用于广泛的色氨酸桥联的多环异吲哚啉酮。该反应代表了一种用于构建复杂桥联多环异吲哚满酮的新颖而有效的方法。此外，进行了几次衍生化以进一步突出此协议的综合价值。
• Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations
  作者：Sivasankaran Dhanasekaran、Arun Suneja、Vishnumaya Bisai、Vinod K. Singh

  DOI：10.1021/acs.orglett.5b03331

  日期：2016.2.19

  A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields.

  据报道，一锅，三组分合成的广泛取代的异吲哚啉酮和异喹啉酮具有路易斯酸催化的有效斯特雷克反应和内酰胺化顺序，可提供高至高收率的产物。该方法还扩展到高产率合成四氢异喹啉（THIQs）。
• Efficient access to (1H)-isoindolin-1-one-3-carboxylic acid derivatives by orthopalladation and carbonylation of methyl arylglycinate substrates
  作者：Sonia Nieto、Francisco J. Sayago、Pedro Laborda、Tatiana Soler、Carlos Cativiela、Esteban P. Urriolabeitia

  DOI：10.1016/j.tet.2011.04.064

  日期：2011.6

  The orthopalladation of methyl arylglycinate derivatives has been studied. The reaction proceeds efficiently for different electron-withdrawing and electron-releasing substituents at the aryl ring. The carbonylation of the orthopalladated complexes affords, in a single step, substituted (1H)-isoindolin-1-one-3-carboxylates. These compounds constitute valuable synthetic intermediates and can be transformed diastereoselectively into octahydroisoindole-1-carboxylic acid derivatives, an important scaffold in the synthesis of many biologically active compounds. (C) 2011 Elsevier Ltd. All rights reserved.