2-[(E)-4-[1-(benzenesulfonyl)indol-3-yl]-2-oxobut-3-enyl]isoindole-1,3-dione | 679005-01-7

• 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-[(E)-4-[1-(benzenesulfonyl)indol-3-yl]-2-oxobut-3-enyl]isoindole-1,3-dione
• CAS: 679005-01-7
• 化学式: C₂₆H₁₈N₂O₅S
• 分子量: 470.505
• InChiKey: KZWBLQKQVAAREJ-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(E)-4-[1-(benzenesulfonyl)indol-3-yl]-2-oxobut-3-enyl]isoindole-1,3-dione 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 27.0h， 生成 7-(1-benzenesulfonyl-1H-indol-3-yl)-2-methyl-4-phthalimido-5-triisopropylsiloxyisoindole-1,3-dione
  参考文献：
  名称：

  Diels–Alder reactivity of 4-aryl-1-phthalimido-2-siloxy-1,3-butadienes

  摘要：

  The reaction of (1Z,3E) and (1E,3E) 4-aryl-1-phthalimido-2-trialkylsiloxy-1,3-butadienes with maleimides and quinones has been studied. The observed exo-stereospecifity can be attributed to the simultaneous presence of the phthalimido and aryl groups, which produce strong hindrance during the endo approach. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.076
• 作为产物：
  描述：

  1-(苯磺酰)-3-吲哚甲醛 、 2-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]-1H-isoindole-1,3(2H)-dione 以 苯 为溶剂， 反应 2.0h， 以79%的产率得到2-[(E)-4-[1-(benzenesulfonyl)indol-3-yl]-2-oxobut-3-enyl]isoindole-1,3-dione
  参考文献：
  名称：

  Diels–Alder reactivity of 4-aryl-1-phthalimido-2-siloxy-1,3-butadienes

  摘要：

  The reaction of (1Z,3E) and (1E,3E) 4-aryl-1-phthalimido-2-trialkylsiloxy-1,3-butadienes with maleimides and quinones has been studied. The observed exo-stereospecifity can be attributed to the simultaneous presence of the phthalimido and aryl groups, which produce strong hindrance during the endo approach. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.076

文献信息

• 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes: synthesis and Diels–Alder reactivity
  作者：Esther Caballero、Dulce Alonso、Rafael Peláez、Concepción Alvarez、Pilar Puebla、Francisca Sanz、Manuel Medarde、Fernando Tomé

  DOI：10.1016/j.tetlet.2003.12.118

  日期：2004.2

  New 1-phthalimido-4-(3-indolyl)-2-trialkylsiloxy-1,3-butadienes were easily prepared from 1,3-dichloropropanone and their configurations were established from NMR data. Their Diels–Alder reactivity with different maleimides and quinones was studied, high yields of the exo cycloadducts being obtained, as confirmed by X-ray diffraction studies.

  新的1-邻苯二甲酰亚胺-4-（3-吲哚基）-2-三烷基甲硅烷氧基-1,3-丁二烯很容易从1,3-二氯丙烷制得，其构型由NMR数据确定。研究了它们与不同的马来酰亚胺和醌的Diels-Alder反应性，通过X射线衍射研究证实，该化合物可得到高产率的exo环加合物。
• Diels–Alder reactivity of 4-aryl-1-phthalimido-2-siloxy-1,3-butadienes
  作者：Esther Caballero、Dulce Alonso、Rafael Peláez、Concepción Álvarez、Pilar Puebla、Francisca Sanz、Manuel Medarde、Fernando Tomé

  DOI：10.1016/j.tet.2005.04.076

  日期：2005.7

  The reaction of (1Z,3E) and (1E,3E) 4-aryl-1-phthalimido-2-trialkylsiloxy-1,3-butadienes with maleimides and quinones has been studied. The observed exo-stereospecifity can be attributed to the simultaneous presence of the phthalimido and aryl groups, which produce strong hindrance during the endo approach. (c) 2005 Elsevier Ltd. All rights reserved.