5-bromoindolyl-3-carbonylnitrile | 444109-01-7

• 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-bromoindolyl-3-carbonylnitrile
• 英文别名: 5-bromo-1H-indole-3-carbonyl cyanide
• CAS: 444109-01-7
• 化学式: C₁₀H₅BrN₂O
• 分子量: 249.066
• InChiKey: BYYZPMCRHNVHOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromoindolyl-3-carbonylnitrile 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 2.5h， 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
• 作为产物：
  描述：

  2-(5-bromo-1H-indol-3-yl)-2-oxoacetamide 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到5-bromoindolyl-3-carbonylnitrile
  参考文献：
  名称：

  A new synthesis of versatile indolyl-3-carbonylnitriles

  摘要：

  Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources Of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible alpha-oxoacetamides in generally high yields under simple reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.075