methyl 4-bromo-(1H)-isoindolin-1-one-3-carboxylate | 1312542-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-bromo-(1H)-isoindolin-1-one-3-carboxylate
• 英文别名: Methyl 7-bromo-3-oxo-1,2-dihydroisoindole-1-carboxylate；methyl 7-bromo-3-oxo-1,2-dihydroisoindole-1-carboxylate
• CAS: 1312542-36-1
• 化学式: C₁₀H₈BrNO₃
• 分子量: 270.082
• InChiKey: BSONAFGTOYAQDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 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

• 作为产物：
  描述：

  DL-2-溴基甘氨酸 在 氯化亚砜 、 palladium diacetate 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 methyl 4-bromo-(1H)-isoindolin-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

文献信息

• 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.