(5Z)-2-(5-bromo-1H-indole-3-carbonyl)-5-[(6-methoxy-1H-indol-3-yl)methylidene]-1H-imidazol-4-one | 444109-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5Z)-2-(5-bromo-1H-indole-3-carbonyl)-5-[(6-methoxy-1H-indol-3-yl)methylidene]-1H-imidazol-4-one
• CAS: 444109-07-3
• 化学式: C₂₂H₁₅BrN₄O₃
• 分子量: 463.29
• InChiKey: UQLKMJNGPJMBKZ-SWNXQHNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 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：
  0.05
• 拓扑面积：
  99.34
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5Z)-2-(5-bromo-1H-indole-3-carbonyl)-5-[(6-methoxy-1H-indol-3-yl)methylidene]-1H-imidazol-4-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 108.0h， 以81%的产率得到rhopaladin A
  参考文献：
  名称：

  Synthesis of the marine alkaloids rhopaladins A, B, C and D

  摘要：

  The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00171-0
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 在 盐酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙醚 为溶剂， 反应 6.0h， 生成 (5Z)-2-(5-bromo-1H-indole-3-carbonyl)-5-[(6-methoxy-1H-indol-3-yl)methylidene]-1H-imidazol-4-one
  参考文献：
  名称：

  Synthesis of the marine alkaloids rhopaladins A, B, C and D

  摘要：

  The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00171-0

文献信息

• Synthesis of the marine alkaloids rhopaladins A, B, C and D
  作者：Tomasz Janosik、Ann-Louise Johnson、Jan Bergman

  DOI：10.1016/s0040-4020(02)00171-0

  日期：2002.4

  The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.