3-butoxypropyl-2-cyanoethylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-butoxypropyl-2-cyanoethylamine
• 英文别名: 3-(3-Butoxypropylamino)propanenitrile；3-(3-butoxypropylamino)propanenitrile
• 化学式: C₁₀H₂₀N₂O
• 分子量: 184.282
• InChiKey: PQOXTGKXVWDMRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine 、 3-butoxypropyl-2-cyanoethylamine 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以25%的产率得到1-(2-ethoxyethyl)-4-(1'-hydroxyethyl)-4-hydroxypiperidine
  参考文献：
  名称：

  A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

  摘要：

  The spirocyclic compounds, 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro[4,5]deca-3-ene and 3-cyano-4-methyl-8-(2-phenylethyl)-1-oxa-8-azaspiro[4.5]dec-3-ene were unexpectedly obtained from the reaction of 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine and 1-(2-phenylethyl)-4-acetyl-4-hydroxypiperidine with acrylonitrile at room temperature in the presence of an alkali catalyst; further hydrolysis led to the corresponding carboxylic acids. The spirocyclic compounds are thought to form via an aldol condensation which follows cyanoethylation. However, the reaction of 3-butoxypropyl-2-cyanoethylamine with 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine leads to 1-(2-ethoxyethyl)-4(1'-hydroxyethyl)-4-hydroxypiperidine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.001
• 作为产物：
  描述：

  3-丁氧基丙胺 、 丙烯腈 以 甲醇 为溶剂， 反应 2.0h， 以69%的产率得到3-butoxypropyl-2-cyanoethylamine
  参考文献：
  名称：

  A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids

  摘要：

  The spirocyclic compounds, 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro[4,5]deca-3-ene and 3-cyano-4-methyl-8-(2-phenylethyl)-1-oxa-8-azaspiro[4.5]dec-3-ene were unexpectedly obtained from the reaction of 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine and 1-(2-phenylethyl)-4-acetyl-4-hydroxypiperidine with acrylonitrile at room temperature in the presence of an alkali catalyst; further hydrolysis led to the corresponding carboxylic acids. The spirocyclic compounds are thought to form via an aldol condensation which follows cyanoethylation. However, the reaction of 3-butoxypropyl-2-cyanoethylamine with 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine leads to 1-(2-ethoxyethyl)-4(1'-hydroxyethyl)-4-hydroxypiperidine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.001

文献信息

• A simple one-pot synthesis of N-substituted 4-methyl-1-oxa-8-azaspiro[4,5]deca-3-en-3-carboxylic acids
  作者：Valentina Yu、Kaldybay Praliyev、Aliya Nagimova、Alexey Zazybin

  DOI：10.1016/j.tetlet.2015.02.001

  日期：2015.3

  The spirocyclic compounds, 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro[4,5]deca-3-ene and 3-cyano-4-methyl-8-(2-phenylethyl)-1-oxa-8-azaspiro[4.5]dec-3-ene were unexpectedly obtained from the reaction of 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine and 1-(2-phenylethyl)-4-acetyl-4-hydroxypiperidine with acrylonitrile at room temperature in the presence of an alkali catalyst; further hydrolysis led to the corresponding carboxylic acids. The spirocyclic compounds are thought to form via an aldol condensation which follows cyanoethylation. However, the reaction of 3-butoxypropyl-2-cyanoethylamine with 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine leads to 1-(2-ethoxyethyl)-4(1'-hydroxyethyl)-4-hydroxypiperidine. (C) 2015 Elsevier Ltd. All rights reserved.