N-((1H-indol-3-yl)(4-hydroxyphenyl)methyl)-N-methylbenzenamine | 1314029-48-5

• 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: N-((1H-indol-3-yl)(4-hydroxyphenyl)methyl)-N-methylbenzenamine
• 英文别名: N-((1H-Indol-3-yl)(4-hydroxy phenyl)methyl)-N-methylbenzenamine；4-[1H-indol-3-yl-(N-methylanilino)methyl]phenol
• CAS: 1314029-48-5
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: PEHAAVNBCZACDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 对羟基苯甲醛 、 N-甲基苯胺 在 3-氯苯硼酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以87%的产率得到N-((1H-indol-3-yl)(4-hydroxyphenyl)methyl)-N-methylbenzenamine
  参考文献：
  名称：

  A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid

  摘要：

  An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3-chlorophenylboronic acid as a catalyst under ambient temperature conditions. The three-component reaction of indoles, aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields. This protocol presents some remarkable features such as mild reaction conditions, simple workup procedure and excellent yields. (C) 2013 Sudhakar R. Bhusare. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.024

文献信息

• 3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities
  作者：V. Kameshwara Rao、Bhupender S. Chhikara、Amir Nasrolahi Shirazi、Rakesh Tiwari、Keykavous Parang、Anil Kumar

  DOI：10.1016/j.bmcl.2011.05.010

  日期：2011.6

  An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf)(3)-SiO2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 mu M. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC50 values of 50.6 and 58.3 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid
  作者：Santosh V. Goswami、Prashant. B. Thorat、Vijay N. Kadam、Sachin A. Khiste、Sudhakar R. Bhusare

  DOI：10.1016/j.cclet.2013.03.024

  日期：2013.5

  An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3-chlorophenylboronic acid as a catalyst under ambient temperature conditions. The three-component reaction of indoles, aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields. This protocol presents some remarkable features such as mild reaction conditions, simple workup procedure and excellent yields. (C) 2013 Sudhakar R. Bhusare. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.