ethyl 2-acetyl-3-methyl-1H-indole-5-carboxylate | 1361091-52-2

• 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: ethyl 2-acetyl-3-methyl-1H-indole-5-carboxylate
• CAS: 1361091-52-2
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: UZHOWPJMLPWUQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-3-methyl-1H-indole-5-carboxylate 在 ammonium acetate 、 phenyltrimethylammonium tribromide 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成
  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：

  2-乙基乙酰乙酸甲酯 、 p-ethyl benzoate diazonium salt 在 sodium hydroxide 、 sodium acetate 、 甲酸 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 以57%的产率得到ethyl 2-acetyl-3-methyl-1H-indole-5-carboxylate
  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

文献信息

• Synthesis and Self-Association of Double-Helical AADD Arrays
  作者：Bhanu P. Mudraboyina、James A. Wisner

  DOI：10.1002/chem.201201668

  日期：2012.10.29

  self‐complementary oligomers that contain an underlying AADD hydrogen bond sequence are presented, and their self‐association was examined in the solution and solid state. The molecular recognition between the two strands is highly sensitive to substitutions of their component heterocycles. Substitution with electron‐donating and ‐withdrawing groups and the influence of preorganization has a large effect on the

  介绍了四个包含基础AADD氢键序列的自互补低聚物的设计和合成，并在溶液和固态下检查了它们的自缔合。两条链之间的分子识别对其组成杂环的取代高度敏感。用给电子和吸电子基团取代以及预组织的影响对所研究复合物的整体稳定性有很大影响。特别地，证明了关于在ADAD低聚物中的各个位置处的取代的宽范围（> 10 5  M -1）的稳定性。在最极端的情况下，测得的二聚常数（K二聚体≥4.5×10 7  M -1）与迄今为止报道的中性AADD阵列最稳定的同型二聚体相当。
• Substituent Effects in Double-Helical Hydrogen-Bonded AAA-DDD Complexes
  作者：Hong-Bo Wang、Bhanu P. Mudraboyina、James A. Wisner

  DOI：10.1002/chem.201103001

  日期：2012.1.27

  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.