1-(cyclohexylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 111328-52-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(cyclohexylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1-cyclohexylmethyl-2,3,4,9-tetrahydro-1H-β-carboline；1-Cyclohexylmethyl-2,3,4,9-tetrahydro-1H-β-carbolin；1-Cyclohexyl-methyl-1,2,3,4-tetrahydro-norharman
• CAS: 111328-52-0
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: VZODOBBKNLHJBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cyclohexyl-acetic acid-(2-indol-3-yl-ethylamide) 在 三氯氧磷 、 苯 作用下， 生成 1-(cyclohexylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Protiva et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 83,86

  摘要：

  DOI：

文献信息

• Biocatalytic asymmetric formation of tetrahydro-β-carbolines
  作者：Peter Bernhardt、Aimee R. Usera、Sarah E. O’Connor

  DOI：10.1016/j.tetlet.2010.06.075

  日期：2010.8

  Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved