N-(2-Cyanoethyl)butanamide | 1118-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2-Cyanoethyl)butanamide
• CAS: 1118-96-3
• 化学式: C₇H₁₂N₂O
• mdl: MFCD16664312
• 分子量: 140.185
• InChiKey: WTPANPSKKAVEQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-Cyanoethyl)butanamide 在 sodium azide 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以300 mg的产率得到3-(5-propyl-1H-tetrazol-1-yl)propanenitrile
  参考文献：
  名称：

  The Conversion of Secondary Amides to Tetrazoles with Trifluoromethanesulfonic Anhydride and Sodium Azide

  摘要：

  由于对四唑作为药物的兴趣，最近推出了一种新的、温和的一步法，使用三苯基膦、偶氮二甲酸二乙酯和三甲基甲硅烷基叠氮化物将酰胺转化为四唑。设计了另一种同样简单的方法，使用三氟甲磺酸酐和叠氮化钠。该方法用于从容易获得的仲酰胺合成一系列 1,5-取代四唑。还通过该方法从被氰乙基保护基取代的酰胺合成了1H-取代的四唑。

  DOI：

  10.1055/s-1993-25934
• 作为产物：
  描述：

  3-氨基-丙腈富马酸盐(1:1) 、 丁酰氯 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-Cyanoethyl)butanamide
  参考文献：
  名称：

  Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole

  摘要：

  5-[4'-Methyl-1,1'-biphenyl-2-yl]-1H-tetrazole (6), which contains a sterically hindered o-tetrazole group, was synthesized by three different routes, one of them employing a new tetrazole synthesis. The first involved the reaction of trialkyltin azides with 4'-methyl-1,1'-biphenyl-2-carbonitrile (3). The resultant trimethyltin-tetrazole adduct could be hydrolyzed with acid to yield biphenylytetrazole 6. The tri-n-butyltin-tetrazole adduct, however, was transformed into the corresponding N-trityl-protected tetrazole 5 to permit removal of the organic soluble tri-n-butyltin byproducts. The trityl group also permits 5 to be brominated at the benzylic position and then alkylated by imidazole derivatives. Subsequent acid hydrolysis of the trityl protecting group of 5 yielded biphenylyltetrazole 6. The second synthesis involved the nitrosation of an N-(2-cyanoethyl)-protected biphenylamidrazone 10 using N2O4 (g) to yield N-(2-cyanoethyl)-protected tetrazole 12. Aqueous base removes the cyanoethyl protecting group to yield biphenylyltetrazole 6. The third method involves the novel transformation of an N-(2-cyanoethyl)-substituted amide into the corresponding N-(2-cyanoethyl)-protected tetrazole in one step using triphenylphosphine, diethyl azodicarboxylate (DEAD), and azidotrimethylsilane. Subsequent base hydrolysis of the cyanoethyl group yielded 6 as before. Examples are also provided of the application of this new reaction to other N-(2-cyanoethyl)-protected carboxamides.

  DOI：

  10.1021/jo00007a027

文献信息

• DUNCIA, JOHN V.;PIERCE, MICHAEL E.;SANTELLA, JOSEPH B. (III), J. ORG. CHEM., 56,(1991) N, C. 2395-2400
  作者：DUNCIA, JOHN V.、PIERCE, MICHAEL E.、SANTELLA, JOSEPH B. (III)

  DOI：——

  日期：——
• Substituted Azaspiro(4.5)Decane Derivatives
  申请人：Gruenenthal GmbH

  公开号：US20170210734A1

  公开（公告）日：2017-07-27

  The invention relates to substituted spirocyclic cyclohexane derivatives which have an affinity for the μ opioid receptor and/or the ORL1 receptor, processes for the preparation thereof, medicaments containing these compounds and the use of these compounds for the preparation of medicaments.
• Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole
  作者：John V. Duncia、Michael E. Pierce、Joseph B. Santella

  DOI：10.1021/jo00007a027

  日期：1991.3

  5-[4'-Methyl-1,1'-biphenyl-2-yl]-1H-tetrazole (6), which contains a sterically hindered o-tetrazole group, was synthesized by three different routes, one of them employing a new tetrazole synthesis. The first involved the reaction of trialkyltin azides with 4'-methyl-1,1'-biphenyl-2-carbonitrile (3). The resultant trimethyltin-tetrazole adduct could be hydrolyzed with acid to yield biphenylytetrazole 6. The tri-n-butyltin-tetrazole adduct, however, was transformed into the corresponding N-trityl-protected tetrazole 5 to permit removal of the organic soluble tri-n-butyltin byproducts. The trityl group also permits 5 to be brominated at the benzylic position and then alkylated by imidazole derivatives. Subsequent acid hydrolysis of the trityl protecting group of 5 yielded biphenylyltetrazole 6. The second synthesis involved the nitrosation of an N-(2-cyanoethyl)-protected biphenylamidrazone 10 using N2O4 (g) to yield N-(2-cyanoethyl)-protected tetrazole 12. Aqueous base removes the cyanoethyl protecting group to yield biphenylyltetrazole 6. The third method involves the novel transformation of an N-(2-cyanoethyl)-substituted amide into the corresponding N-(2-cyanoethyl)-protected tetrazole in one step using triphenylphosphine, diethyl azodicarboxylate (DEAD), and azidotrimethylsilane. Subsequent base hydrolysis of the cyanoethyl group yielded 6 as before. Examples are also provided of the application of this new reaction to other N-(2-cyanoethyl)-protected carboxamides.
• The Conversion of Secondary Amides to Tetrazoles with Trifluoromethanesulfonic Anhydride and Sodium Azide
  作者：Edward W. Thomas

  DOI：10.1055/s-1993-25934

  日期：——

  Due to the interest in tetrazoles as medicinal agents, a new, mild one-step method for the conversion of amides to tetrazoles employing triphenylphosphine, diethyl azodicarboxylate, and trimethylsilyl azide was recently introduced. An alternate and equally simple method employing trifluoromethanesulfonic anhydride and sodium azide was devised. This method was used to synthesize a series of 1,5-substituted tetrazoles from readily available secondary amides. A 1H-substituted tetrazole was also synthesized by this method from an amide substituted with a cyanoethyl protecting group.

  由于对四唑作为药物的兴趣，最近推出了一种新的、温和的一步法，使用三苯基膦、偶氮二甲酸二乙酯和三甲基甲硅烷基叠氮化物将酰胺转化为四唑。设计了另一种同样简单的方法，使用三氟甲磺酸酐和叠氮化钠。该方法用于从容易获得的仲酰胺合成一系列 1,5-取代四唑。还通过该方法从被氰乙基保护基取代的酰胺合成了1H-取代的四唑。