cis-1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

• 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: cis-1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 化学式: C₁₉H₁₇IN₂O₂
• 分子量: 432.261
• InChiKey: VXYSOJPQDXRUIC-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  丙二烯 、 cis-1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以77%的产率得到methyl (1S,12S)-15-methylidene-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16,18,20-heptaene-12-carboxylate
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1
• 作为产物：
  描述：

  2-碘苯甲醛 在 magnesium sulfate 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 cis-1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1

文献信息

• Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan、Mark Thornton-Pett、Jin Zhang

  DOI：10.1016/s0040-4020(00)00628-1

  日期：2000.8

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.