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.