2-acetyl-3-methyl-1H-indole-5-carbonitrile | 1361091-56-6

• 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: 2-acetyl-3-methyl-1H-indole-5-carbonitrile
• CAS: 1361091-56-6
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: NUCNXCDWFROZQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.65
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-methyl-1H-indole-5-carbonitrile 在 半胱胺盐酸盐 、 phenyltrimethylammonium tribromide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.5h， 生成 2-(2-mercaptoacetyl)-3-methyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Substituent Effects in Double-Helical Hydrogen-Bonded AAA-DDD Complexes

  摘要：

  AbstractTwo series of DDD and AAA hydrogen‐bond arrays were synthesized that form triply‐hydrogen‐bonded double‐helical complexes when combined in CDCl3 solution. Derivatization of the DDD arrays with electron‐withdrawing groups increases the complex association constants by up to a factor of 30 in those arrays examined. Derivatization of the AAA arrays with electron donating substituents reveals a similar magnitude effect on the complex stabilities. The effect of substitution on both types of arrays are modeled quite satisfactorily (R2 > 0.96 in all cases) as free energy relationships with respect to the sums of their Hammett substituent constants. In all, the complex stabilities can be manipulated over more than three orders of magnitude (>20 kJ mol−1) using this type of modification.

  DOI：

  10.1002/chem.201103001
• 作为产物：
  描述：

  4-bromo-benzenediazonium ion 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 2-acetyl-3-methyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Substituent Effects in Double-Helical Hydrogen-Bonded AAA-DDD Complexes

  摘要：

  AbstractTwo series of DDD and AAA hydrogen‐bond arrays were synthesized that form triply‐hydrogen‐bonded double‐helical complexes when combined in CDCl3 solution. Derivatization of the DDD arrays with electron‐withdrawing groups increases the complex association constants by up to a factor of 30 in those arrays examined. Derivatization of the AAA arrays with electron donating substituents reveals a similar magnitude effect on the complex stabilities. The effect of substitution on both types of arrays are modeled quite satisfactorily (R2 > 0.96 in all cases) as free energy relationships with respect to the sums of their Hammett substituent constants. In all, the complex stabilities can be manipulated over more than three orders of magnitude (>20 kJ mol−1) using this type of modification.

  DOI：

  10.1002/chem.201103001