1-(2-iodo-phenyl)-2-thienylmethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 303744-29-8

• 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-(2-iodo-phenyl)-2-thienylmethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,3S)-1-(2-iodophenyl)-2-(thiophen-2-ylmethyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 303744-29-8
• 化学式: C₂₄H₂₁IN₂O₂S
• 分子量: 528.413
• InChiKey: JBRJTCUBOBDQIG-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  丙二烯 、 1-(2-iodo-phenyl)-2-thienylmethyl-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 40.0h， 以48%的产率得到methyl (10S,12R)-19-methylidene-11-(thiophen-2-ylmethyl)-1,11-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-2,4,6,8(21),13,15,17-heptaene-10-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：

  3-(1H-indol-3-yl)-2-(thiophen-2-ylmethyleneamino)propionic acid methyl ester 在 三乙酰氧基硼氢化钠 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 40.0h， 生成 1-(2-iodo-phenyl)-2-thienylmethyl-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.