3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole | 146886-61-5

• 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: 3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole
• 英文别名: 4-amino-1-(triisopropylsilyl)gramine；3-[(Dimethylamino)methyl]-1-tri(propan-2-yl)silylindol-4-amine
• CAS: 146886-61-5
• 化学式: C₂₀H₃₅N₃Si
• 分子量: 345.603
• InChiKey: ZVVKFNNTEBECPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole 在 palladium on activated charcoal 、 四(三苯基膦)钯 、 penicillin G acyalse 吗啉 、 N-甲基吗啉 、 2,6-二甲基吡啶 、 甲醇 、 sodium hydroxide 、 锂硼氢 、 四丁基氟化铵 、 水 、 氢气 、 氢气 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Natural Product Synthesis on Polymeric Supports—Synthesis and Biological Evaluation of an Indolactam Library

  摘要：

  Potent activators of protein kinase C in fibroblasts: This property was determined for several indolactam V analogues (1) with a new cell-based assay system. This tumor-promoting indole alkaloid and analogues thereof can be synthesized efficiently on the solid phase. The key steps of the combinatorial approach are a regioselective amination of the indole ring and an enantioselective enzymatic reaction.

  DOI：

  10.1002/(sici)1521-3773(19991004)38:19<2902::aid-anie2902>3.0.co;2-2
• 作为产物：
  描述：

  芦竹碱 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.75h， 生成 3-Dimethylaminomethyl-4-amino-1-triisopropylsilylindole
  参考文献：
  名称：

  10.1002/1521-3765(20001103)6:21<3943::aid-chem3943<3.3.co;2-k

  摘要：

  DOI：

  10.1002/1521-3765(20001103)6:21<3943::aid-chem3943<3.3.co;2-k

文献信息

• Directed Lithiation of 1-Triisopropylsilylgramine. A Short Access to 3,4-Disubstituted Indoles
  作者：Masatomo Iwao

  DOI：10.3987/com-92-6185

  日期：——

  1-Triisopropylsilylgramine was lithiated regioselectively at C-4 by treatment with t-BuLi in ether at 0-degrees-C for 1 h. The lithiated species was trapped with a variety of electrophiles to furnish 4-functionalized gramine derivatives in good yields. Replacement of the triisopropylsilyl protecting group by a methyl group resulted in C-2 selective lithiation under the similar reaction conditions.
• 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.
• Natural Product Synthesis on Polymeric Supports—Synthesis and Biological Evaluation of an Indolactam Library
  作者：Benjamin Meseguer、Daniel Alonso-Díaz、Nils Griebenow、Thomas Herget、Herbert Waldmann

  DOI：10.1002/(sici)1521-3773(19991004)38:19<2902::aid-anie2902>3.0.co;2-2

  日期：1999.10.4

  Potent activators of protein kinase C in fibroblasts: This property was determined for several indolactam V analogues (1) with a new cell-based assay system. This tumor-promoting indole alkaloid and analogues thereof can be synthesized efficiently on the solid phase. The key steps of the combinatorial approach are a regioselective amination of the indole ring and an enantioselective enzymatic reaction.
• 10.1002/1521-3765(20001103)6:21<3943::aid-chem3943<3.3.co;2-k
  作者：Meseguer, Benjamin、Alonso-Diaz, Daniel、Griebenow, Nils、Herget, Thomas、Waldmann, Herbert

  DOI：10.1002/1521-3765(20001103)6:21<3943::aid-chem3943<3.3.co;2-k

  日期：——