[2-(2,3-dihydro-1H-indol-1-yl)ethyl](methyl)amine | 1021015-67-7

• 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: [2-(2,3-dihydro-1H-indol-1-yl)ethyl](methyl)amine
• 英文别名: 2-(2,3-dihydroindol-1-yl)-N-methylethanamine
• CAS: 1021015-67-7
• 化学式: C₁₁H₁₆N₂
• mdl: MFCD11155243
• 分子量: 176.261
• InChiKey: BJKQSFDKXBILAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-(2,3-dihydro-1H-indol-1-yl)ethyl](methyl)amine 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling

  摘要：

  The activity of four native FDHs and four engineered FDH variants on 93 low-molecular-weight arenes was used to generate FDH substrate activity profiles. These profiles provided insights into how substrate class, functional group substitution, electronic activation, and binding affect FDH activity and selectivity. The enzymes studied could halogenate a far greater range of substrates than have been previously recognized, but significant differences in their substrate specificity and selectivity were observed. Trends between the electronic activation of each site on a substrate and halogenation conversion at that site were established, and these data, combined with docking simulations, suggest that substrate binding can override electronic activation even on compounds differing appreciably from native substrates. These findings provide a useful framework for understanding and exploiting FDH reactivity for organic synthesis.

  DOI：

  10.1021/acscatal.6b02707
• 作为产物：
  描述：

  3-甲基-2-恶唑烷酮 、 吲哚啉 在 水 、 potassium hydroxide 作用下， 反应 10.0h， 生成 [2-(2,3-dihydro-1H-indol-1-yl)ethyl](methyl)amine
  参考文献：
  名称：

  Me 3 SiCl促进的芳香化合物与N，O-缩醛束缚的分子内环化反应，可轻松制备1,4-苯并二氮杂pine骨架

  摘要：

  Me 3 SiCl促进的新型N，O-乙缩醛的分子内氨甲基化反应，是由N-烷基苯胺衍生物和N-烷基-2-恶唑烷酮通过容易的三步合成法制备的，可生产药学上有用的物质描述了具有各种官能团的1，4-苯并二氮杂skeleton骨架。此方法经7-成功地应用于两个三环苯并二氮杂衍生物的制备容易和1,4-苯并氧氮杂衍生物外切- trig的环化。

  DOI：

  10.1016/j.tet.2010.09.077

文献信息

• Understanding Flavin-Dependent Halogenase Reactivity via Substrate Activity Profiling
  作者：Mary C. Andorfer、Jonathan E. Grob、Christine E. Hajdin、Julia R. Chael、Piro Siuti、Jeremiah Lilly、Kian L. Tan、Jared C. Lewis

  DOI：10.1021/acscatal.6b02707

  日期：2017.3.3

  The activity of four native FDHs and four engineered FDH variants on 93 low-molecular-weight arenes was used to generate FDH substrate activity profiles. These profiles provided insights into how substrate class, functional group substitution, electronic activation, and binding affect FDH activity and selectivity. The enzymes studied could halogenate a far greater range of substrates than have been previously recognized, but significant differences in their substrate specificity and selectivity were observed. Trends between the electronic activation of each site on a substrate and halogenation conversion at that site were established, and these data, combined with docking simulations, suggest that substrate binding can override electronic activation even on compounds differing appreciably from native substrates. These findings provide a useful framework for understanding and exploiting FDH reactivity for organic synthesis.
• Me3SiCl-promoted intramolecular cyclization of aromatic compounds tethered with N,O-acetals leading to the facile preparation of 1,4-benzodiazepine skeletons
  作者：Norio Sakai、Akimasa Watanabe、Reiko Ikeda、Yumi Nakaike、Takeo Konakahara

  DOI：10.1016/j.tet.2010.09.077

  日期：2010.11

  synthesis from N-alkylaniline derivatives and N-alkyl-2-oxazolidinones that leads to the production of pharmaceutically useful 1,4-benzodiazepine skeletons with a variety of functional groups is described. This method was successfully applied to the facile preparation of both tricyclic benzodiazepine derivatives and a 1,4-benzoxazepine derivative via 7-exo-trig cyclization.

  Me 3 SiCl促进的新型N，O-乙缩醛的分子内氨甲基化反应，是由N-烷基苯胺衍生物和N-烷基-2-恶唑烷酮通过容易的三步合成法制备的，可生产药学上有用的物质描述了具有各种官能团的1，4-苯并二氮杂skeleton骨架。此方法经7-成功地应用于两个三环苯并二氮杂衍生物的制备容易和1,4-苯并氧氮杂衍生物外切- trig的环化。