5-[1-[2-(trimethylsilyl)ethoxymethyl]indol-2-yl]pyran-2-one | 217448-42-5

• 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: 5-[1-[2-(trimethylsilyl)ethoxymethyl]indol-2-yl]pyran-2-one
• 英文别名: 5-[1-(2-Trimethylsilylethoxymethyl)indol-2-yl]pyran-2-one
• CAS: 217448-42-5
• 化学式: C₁₉H₂₃NO₃Si
• 分子量: 341.482
• InChiKey: HPDHKPXBPJQZCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[1-[2-(trimethylsilyl)ethoxymethyl]indol-2-yl]pyran-2-one 在 Eu(fod)3 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 6-ethoxy-4-hydroxy-3-[1-[2-(trimethylsilyl)ethoxymethyl]indol-2-yl]cyclohex-2-ene carboxylic acid 2,2-dimethoxyethyl amide
  参考文献：
  名称：

  Diastereoselective Diels–Alder Reaction of 5-(Indol-2-yl)-pyran-2-one

  摘要：

  5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and electron-rich dienophiles. Lanthanide shift reagents have been shown to be efficient catalysts for the inverse electron demand Diels-Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of bicycloadducts with primary amines is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00183-6
• 作为产物：
  描述：

  1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-吲哚 在 正丁基锂 、 三甲基氯硅烷 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 生成 5-[1-[2-(trimethylsilyl)ethoxymethyl]indol-2-yl]pyran-2-one
  参考文献：
  名称：

  Application of the Pd-catalyzed heteroarylation to the synthesis of 5-(indol-2′-yl)pyridin-2-one and 5-(indol-2′-yl)pyran-2-one

  摘要：

  The synthesis of 5-(indol-2'-yl)pyridin-2-ones and 5-(indol-2'-yl)pyran-2-one by Pd-catalyzed reactions is described. The best results are obtained using 2-indolylstannanes or 2-indolylzinc halides to be coupled with 5-bromopyridin-2-ones or 5-bromopyran-2-one in the presence of Pd(PPh3)(4) catalyst. Other Pd-catalyzed reactions are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00858-8

文献信息

• Application of the Pd-catalyzed heteroarylation to the synthesis of 5-(indol-2′-yl)pyridin-2-one and 5-(indol-2′-yl)pyran-2-one
  作者：Bruno Danieli、Giordano Lesma、Marisa Martinelli、Daniele Passarella、Ilaria Peretto、Alessandra Silvani

  DOI：10.1016/s0040-4020(98)00858-8

  日期：1998.11

  The synthesis of 5-(indol-2'-yl)pyridin-2-ones and 5-(indol-2'-yl)pyran-2-one by Pd-catalyzed reactions is described. The best results are obtained using 2-indolylstannanes or 2-indolylzinc halides to be coupled with 5-bromopyridin-2-ones or 5-bromopyran-2-one in the presence of Pd(PPh3)(4) catalyst. Other Pd-catalyzed reactions are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Diels–Alder Reaction of 5-(Indol-2-yl)-pyran-2-one
  作者：Daniele Passarella、Giordano Lesma、Marisa Martinelli、Alessandra Silvani、Margalida Cantò、Josè Hidalgo

  DOI：10.1016/s0040-4020(00)00183-6

  日期：2000.7

  5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and electron-rich dienophiles. Lanthanide shift reagents have been shown to be efficient catalysts for the inverse electron demand Diels-Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of bicycloadducts with primary amines is described. (C) 2000 Elsevier Science Ltd. All rights reserved.