4-[(2-Ethylphenyl)hydrazinylidene]butan-1-ol | 1226954-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(2-Ethylphenyl)hydrazinylidene]butan-1-ol
• CAS: 1226954-31-9
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: BVRLGLJZJOMPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-Ethylphenyl)hydrazinylidene]butan-1-ol 在 硫酸 作用下， 以 水 为溶剂， 生成 7-乙基-3-羟乙基吲哚 、 7-ethyltryptophol 、 2-(8-Ethylcinnolin-4-yl)ethanol
  参考文献：
  名称：

  A Continuous Kilogram-Scale Process for the Manufacture of 7-Ethyltryptophol

  摘要：

  An expeditious and multikilogram-scale process for the synthesis of 7-ethyltryptophol via a continuous flow reactor from 2-ethylphenylhydrazine and 4-hydroxybutyraldehyde in higher and high yield was described. The main steps in this synthesis involved not only the generation of the hydrazone intermediate in situ but also the catalysis of the subsequent [3 + 3] sigmatropic rearrangement in the tandem loop reactor. Decomposition of the intermediate hydrazone was found to be a key factor resulting in low yield.

  DOI：

  10.1021/op1003083
• 作为产物：
  描述：

  4-羟基丁醛 、 邻乙基苯肼盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 4-[(2-Ethylphenyl)hydrazinylidene]butan-1-ol
  参考文献：
  名称：

  A Continuous Kilogram-Scale Process for the Manufacture of 7-Ethyltryptophol

  摘要：

  An expeditious and multikilogram-scale process for the synthesis of 7-ethyltryptophol via a continuous flow reactor from 2-ethylphenylhydrazine and 4-hydroxybutyraldehyde in higher and high yield was described. The main steps in this synthesis involved not only the generation of the hydrazone intermediate in situ but also the catalysis of the subsequent [3 + 3] sigmatropic rearrangement in the tandem loop reactor. Decomposition of the intermediate hydrazone was found to be a key factor resulting in low yield.

  DOI：

  10.1021/op1003083

文献信息

• On the Fischer Indole Synthesis of 7-Ethyltryptophol—Mechanistic and Process Intensification Studies under Continuous Flow Conditions
  作者：Bernhard Gutmann、Michael Gottsponer、Petteri Elsner、David Cantillo、Dominique M. Roberge、C. Oliver Kappe

  DOI：10.1021/op300363s

  日期：2013.2.15

  7-Ethyltryptophol, a key intermediate in the synthesis of the anti-inflammatory agent etodolac, was produced by Fischer indole synthesis of 2-ethylphenylhydrazine and 2,3-dihydrofuran under continuous flow conditions. The reaction generates several undesired byproducts and therefore product yields could not be improved above 40–50%. The mechanism of this transformation was studied in detail and the

  抗炎剂依托度酸合成中的关键中间体7-乙炔酚，是在连续流动条件下通过费歇尔吲哚合成2-乙基苯基肼和2,3-二氢呋喃制得的。该反应产生了几种不希望有的副产物，因此产物收率不能提高到40-50％以上。详细研究了这种转化的机理，并仔细阐明了副产物的结构。尽管只有中等程度的产物收率，但是与替代方法相比，通过该方案进行的7-乙基色酚的合成仍然令人感兴趣，并且是从廉价的试剂开始的。所开发的方法在环境友好的溶剂（甲醇）中进行，重要的是，可以通过直接提取方法从7-乙基色酚产物中除去大部分副产物。