ethyl 3-methyl-2-propanoyl-1H-indole-5-carboxylate | 1361091-53-3

• 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 3-methyl-2-propanoyl-1H-indole-5-carboxylate
• CAS: 1361091-53-3
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: OZWBLMJWDMTDCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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 3-methyl-2-propanoyl-1H-indole-5-carboxylate 在 phenyltrimethylammonium tribromide 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.5h， 生成 ethyl 2-(2-((1-(5-(ethoxycarbonyl)-3-methyl-1H-indol-2-yl)-1-oxopropan-2-yl)thio)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
• 作为产物：
  描述：

  2-乙基-3-氧代戊酸甲酯 、 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54%的产率得到ethyl 3-methyl-2-propanoyl-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

• 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.