11-Bromo-4,5-dimethoxy-8-oxo-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaene-10-carboxylic acid | 1367360-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 11-Bromo-4,5-dimethoxy-8-oxo-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaene-10-carboxylic acid
• 英文别名: 11-bromo-4,5-dimethoxy-8-oxo-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaene-10-carboxylic acid
• CAS: 1367360-15-3
• 化学式: C₁₈H₁₂BrNO₅
• 分子量: 402.201
• InChiKey: KJSWTGJIMKDPET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11-Bromo-4,5-dimethoxy-8-oxo-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaene-10-carboxylic acid 在 碘苯二乙酸 、 lithium bromide 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 3.0h， 以69%的产率得到10,11-Dibromo-4,5-dimethoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaen-8-one
  参考文献：
  名称：

  Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction

  摘要：

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.132
• 作为产物：
  描述：

  7H-9,10-dimethoxypyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid 在 碘苯二乙酸 、 potassium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以75%的产率得到11-Bromo-4,5-dimethoxy-8-oxo-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,10,12,14-heptaene-10-carboxylic acid
  参考文献：
  名称：

  Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction

  摘要：

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.132

文献信息

• Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction
  作者：Yasuyoshi Miki、Hideaki Umemoto、Masashi Dohshita、Hiromi Hamamoto

  DOI：10.1016/j.tetlet.2012.01.132

  日期：2012.4

  The treatment of 8,9,10-trimethoxy-7H-pyrrolo[3,2,1-de]phenanthridine-4,5-dicarboxylic acid with phenyliodine diacetate and potassium iodide in tetrahydrofuran gave the corresponding 4,5-diiodo derivative, which was converted to kalbretorine via reduction, demethylation, followed by alkylation. (C) 2012 Elsevier Ltd. All rights reserved.