methyl (3S)-1-(4-chlorophenyl)-2-(2-nitrophenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate | 865619-30-3

• 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: methyl (3S)-1-(4-chlorophenyl)-2-(2-nitrophenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 865619-30-3
• 化学式: C₂₅H₂₀ClN₃O₄
• 分子量: 461.904
• InChiKey: VFWRNRJXTAARGD-OWJIYDKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S)-1-(4-chlorophenyl)-2-(2-nitrophenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以71%的产率得到(1S)-12-(4-chlorophenyl)-10,13,20-triazapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-3(11),4,6,8,14,16,18-heptaen-21-one
  参考文献：
  名称：

  Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids

  摘要：

  Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-beta-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBUSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-beta-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-beta-carbolinequinoxalinones was unprecedented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.153
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 4-二甲氨基吡啶 作用下， 以 三氟乙酸 为溶剂， 反应 4.7h， 生成 methyl (3S)-1-(4-chlorophenyl)-2-(2-nitrophenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids

  摘要：

  Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-beta-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBUSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-beta-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-beta-carbolinequinoxalinones was unprecedented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.153

文献信息

• Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids
  作者：Ming-Chung Tseng、Yang-Min Liang、Yen-Ho Chu

  DOI：10.1016/j.tetlet.2005.06.153

  日期：2005.9

  Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-beta-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBUSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-beta-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-beta-carbolinequinoxalinones was unprecedented. (c) 2005 Elsevier Ltd. All rights reserved.