3-tert-butoxycarbonylmethyl-5-methyl-2-tosylisoindolin-1-one | 1267588-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-tert-butoxycarbonylmethyl-5-methyl-2-tosylisoindolin-1-one
• 英文别名: tert-butyl 2-[6-methyl-2-(4-methylphenyl)sulfonyl-3-oxo-1H-isoindol-1-yl]acetate
• CAS: 1267588-29-3
• 化学式: C₂₂H₂₅NO₅S
• 分子量: 415.51
• InChiKey: YFGNOBXTIYERBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 、 4-甲基-N-[(4-甲基苯基)磺酰基]苯甲酰胺 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到3-tert-butoxycarbonylmethyl-5-methyl-2-tosylisoindolin-1-one
  参考文献：
  名称：

  Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides

  摘要：

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.095

文献信息

• <i>N</i>-Acylsulfonamide Assisted Tandem C−H Olefination/Annulation: Synthesis of Isoindolinones
  作者：Chen Zhu、J. R. Falck

  DOI：10.1021/ol200093f

  日期：2011.3.4

  A tandem C-H olefination/annulation sequence directed by N-acylsulfonamides affords a variety of isoindolinones. This transformation is compatible with aliphatic alkenes as well as conjugated alkenes. Notably, molecular oxygen can be used as the sole, eco-friendly oxidant.
• Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides
  作者：Chen Zhu、John R. Falck

  DOI：10.1016/j.tet.2012.08.095

  日期：2012.11

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.