5-Benzyloxy-3-(dimethylaminopropyl)-indol | 1163-50-4

• 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-Benzyloxy-3-(dimethylaminopropyl)-indol
• 英文别名: N,N-dimethyl-3-(5-phenylmethoxy-1H-indol-3-yl)propan-1-amine
• CAS: 1163-50-4
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: QAMMMHPYPGIPLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-苄氧基吲哚 在 三乙酰氧基硼氢化钠 、 (2S,5S)-(-)-2-叔丁基-3-甲基-5-苯基-4-咪唑啉酮 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 生成 5-Benzyloxy-3-(dimethylaminopropyl)-indol
  参考文献：
  名称：

  Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)

  摘要：

  A series of N,N-dimethylhomotryptamines was prepared and their binding affinities at the serotonin transporter (SERT) were determined. Compounds possessing an electron withdrawing substituent at the C5-position of the indole nucleus were found to be potent SSRIs. Initial attempts at conformational restriction of the propylamine sidechain by incorporation of a quinuclidine bicyclic structure did not improve binding affinity at SERT. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.059

文献信息

• One-pot synthesis of homotryptamines from indoles
  作者：Derek J. Denhart、Ronald J. Mattson、Jonathan L. Ditta、John E. Macor

  DOI：10.1016/j.tetlet.2004.03.070

  日期：2004.5

  A method is presented for the one-pot synthesis of homotryptamines by the MacMillan reaction of indoles with acrolein followed by reductive amination. (C) 2004 Elsevier Ltd. All rights reserved.
• Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)
  作者：William D. Schmitz、Derek J. Denhart、Allison B. Brenner、Jonathan L. Ditta、Ronald J. Mattson、Gail K. Mattson、Thaddeus F. Molski、John E. Macor

  DOI：10.1016/j.bmcl.2005.01.059

  日期：2005.3

  A series of N,N-dimethylhomotryptamines was prepared and their binding affinities at the serotonin transporter (SERT) were determined. Compounds possessing an electron withdrawing substituent at the C5-position of the indole nucleus were found to be potent SSRIs. Initial attempts at conformational restriction of the propylamine sidechain by incorporation of a quinuclidine bicyclic structure did not improve binding affinity at SERT. (c) 2005 Elsevier Ltd. All rights reserved.