4-(N-tert-butoxycarbonyl)amino-5-(N,N-diethylcarbamoyl)-1-(triisopropylsilyl)gramine

• 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: 4-(N-tert-butoxycarbonyl)amino-5-(N,N-diethylcarbamoyl)-1-(triisopropylsilyl)gramine
• 英文别名: tert-butyl N-[5-(diethylcarbamoyl)-3-[(dimethylamino)methyl]-1-tri(propan-2-yl)silylindol-4-yl]carbamate
• 化学式: C₃₀H₅₂N₄O₃Si
• 分子量: 544.853
• InChiKey: KMJJFWYFPHKKIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(triisopropylsilyl)gramine 在 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 6.75h， 生成 4-(N-tert-butoxycarbonyl)amino-5-(N,N-diethylcarbamoyl)-1-(triisopropylsilyl)gramine
  参考文献：
  名称：

  Synthesis of 3,4,5-trisubstituted indoles via iterative directed lithiation of 1-(triisopropylsilyl)gramines

  摘要：

  Directed lithiation of 1-(triisopropylsilyl)gramines 1 with tert-butyl lithium followed by reaction with trimethylsilylmethyl azide produced 4-amino-1-(triisopropylsilyl)gramines 7. The N-tert-butoxycarbonyl derivatives 8 were lithiated selectively at C-5 with tert-butyllithium and the lithiated species were reacted with a variety of electrophiles to give 5-functionalized compounds, 9 and 10. A facile method to produce 3,4,5-trisubstituted indoles from readily available gramine derivatives is thereby established. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.064

文献信息

• Synthesis of 3,4,5-trisubstituted indoles via iterative directed lithiation of 1-(triisopropylsilyl)gramines
  作者：Tsutomu Fukuda、Hiroko Akashima、Masatomo Iwao

  DOI：10.1016/j.tet.2005.04.064

  日期：2005.7

  Directed lithiation of 1-(triisopropylsilyl)gramines 1 with tert-butyl lithium followed by reaction with trimethylsilylmethyl azide produced 4-amino-1-(triisopropylsilyl)gramines 7. The N-tert-butoxycarbonyl derivatives 8 were lithiated selectively at C-5 with tert-butyllithium and the lithiated species were reacted with a variety of electrophiles to give 5-functionalized compounds, 9 and 10. A facile method to produce 3,4,5-trisubstituted indoles from readily available gramine derivatives is thereby established. (c) 2005 Elsevier Ltd. All rights reserved.