5-bromo-7-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline | 129968-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromo-7-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 5-bromo-7-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-one；5-Bromo-7-methoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• CAS: 129968-02-1
• 化学式: C₁₂H₁₁BrN₂O₂
• 分子量: 295.136
• InChiKey: GKTLTRIRKNQLDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-7-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 在 硼烷 作用下， 生成 5-Bromo-7-methoxy-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Binding of β-carbolines at imidazoline I 2 receptors: a structure–affinity investigation

  摘要：

  A series of ring-substituted (i.e., methoxy and bromo) 3,4-dihydro- and 1,2,3,4-tetrahydro-beta-carbolines was examined at 12 imidazoline receptors, as was the effect of ring-opening, ring-expansion, and translocation of the piperidinyl nitrogen atom. Several analogues were identified that bind with K-i < 20 nM at I-2 sites and with reduced affinity at alpha(2)-adrenergic receptors, and 1,2,3,4-tetrahydro-gamma-carbolines were identified as a novel class of I-2 imidazoline receptor ligand. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.078
• 作为产物：
  描述：

  2,3-piperidinedione 3-(5'-methoxy-2'-bromophenyl)hydrazone 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以20%的产率得到5-bromo-7-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro-.beta.-carbolines from tryptamine-2-carboxylic acids

  摘要：

  The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-beta-carbolines 14a-j in good to excellent yields. This reaction greatly enhances the use of the Abramovitch-Shapiro method for the synthesis of highly oxygenated ring A substituted 1,2,3,4-tetrahydro-beta-carbolines (THBC). The lactams 14f,g and 14h are key intermediates for the synthesis of ring A substituted 1-methoxycanthin-6-one analogues.

  DOI：

  10.1021/jo00001a066

文献信息

• NARAYANAN, KRISHNASWAMY;SCHINDLER, LIESL;COOK, JAMES M., J. ORG. CHEM., 56,(1991) N, C. 359-365
  作者：NARAYANAN, KRISHNASWAMY、SCHINDLER, LIESL、COOK, JAMES M.

  DOI：——

  日期：——