3-(2-(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethyl)-1H-indole-5-carbonitrile | 1217353-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3-(2-(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethyl)-1H-indole-5-carbonitrile
• 英文别名: 3-[2-(2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)ethyl]-1H-indole-5-carbonitrile
• CAS: 1217353-35-9
• 化学式: C₂₁H₂₁N₃
• 分子量: 315.418
• InChiKey: PQVFTFGHDAAJKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethyl)-1H-indole-5-carbonitrile 在 二乙胺 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 、
  参考文献：
  名称：

  Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo [3+2] dipolar cycloaddition with cyclic nitrones to afford substituted isoxazoles in good yield and high diastereoselectivity. The cycloadducts were readily converted in 4 steps into ring constrained homotryptamine analogs. These analogs exhibited excellent binding affinity for the human serotonin transporter (hSERT). Indoles bearing a 5-cyano group and a pendent ethyl(tetrahydroisoquinoline) moiety at the 3-position displayed the best potency for hSERT and high selectivity versus hDAT and hNET. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.043
• 作为产物：
  描述：

  在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo [3+2] dipolar cycloaddition with cyclic nitrones to afford substituted isoxazoles in good yield and high diastereoselectivity. The cycloadducts were readily converted in 4 steps into ring constrained homotryptamine analogs. These analogs exhibited excellent binding affinity for the human serotonin transporter (hSERT). Indoles bearing a 5-cyano group and a pendent ethyl(tetrahydroisoquinoline) moiety at the 3-position displayed the best potency for hSERT and high selectivity versus hDAT and hNET. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.043