N-(5-methylpyrid-2-yl) cyanoacetamide | 132371-13-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-methylpyrid-2-yl) cyanoacetamide
• 英文别名: N-(5-Methyl-2-pyridyl)cyanoacetamide；2-cyano-N-(5-methylpyridin-2-yl)acetamide
• CAS: 132371-13-2
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: XHKAOIJKVADEKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-methylpyrid-2-yl) cyanoacetamide 在 乙醚 、 (butane-1-sulfenyl)-dibutyl-borane 作用下， 生成 N,N'-di(5-methylpyrid-2-yl) 3-amino-2-cyanopenten-2-ene-1,5-diamide
  参考文献：
  名称：

  Dimerization of N-(pyrid-2-YL)- and N-(5-methylpyrid-2-YL) cyanoacetamides by the action of butylthiodibutylborane

  摘要：

  The reaction of N-(pyrid-2-yl) and N-(5-methylpyrid-2-yl) cyanoacetamides with butylthiodibutylborane in a 2:3 ratio leads to the formation of trinuclear complex boron compounds, the alcoholysis of which gave N,N'-di(pyrid-2-yl) 3-amino-2-cyanopent-2-ene-1,5-diamides. The latter are dimers of the starting cyanamides, which are capable of acting as hexadentate chelating agents.

  DOI：

  10.1007/bf00959648
• 作为产物：
  描述：

  4-Amino-7-methyl-2H-pyrido<1,2-a>pyrimidin-2-one 150.0~155.0 ℃ 、266.64 Pa 条件下， 以83%的产率得到N-(5-methylpyrid-2-yl) cyanoacetamide
  参考文献：
  名称：

  Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine

  摘要：

  The reaction of 2-aminopyridine and 2-aminopicolines with ethyl cyanoacetate under high pressures results in the formation of 4-amino-4H-pyrido[1,2-a]pyrimidin-2-ones. Depending on the structure of the initial pyridine base, heating of a mixture of the above reagents under low vacuum gives either the same products or their isomeric N-(2-pyridyl)cyanoacetamideBARs. The mutual transformations of the synthesized isomers were studied; it was found that cyanoacetamides are readily cyclized by the action of an alcoholic solution of HCl into pyrido[1,2-a]pyrimidin-2-ones, while the latter, during sublimation or heating in DMSO, undergo opening of the pyrimidine ring.

  DOI：

  10.1007/bf00958262

文献信息

• Development of quinazolinone and vanillin acrylamide hybrids as multi-target directed ligands against Alzheimer’s disease and mechanistic insights into their binding with acetylcholinesterase
  作者：Kandrakonda Yelamanda Rao、Shaik Jeelan Basha、Kallubai Monika、Navya Naidu Gajula、Irla Sivakumar、Sandeep Kumar、Ramakrishna Vadde、Bindu Madhava Reddy Aramati、Rajagopal Subramanyam、Amooru Gangaiah Damu

  DOI：10.1080/07391102.2023.2203255

  日期：2023.12.21

  In view of Multi-Target Directed Ligand (MTDL) approach in treating Alzheimer’s Disease (AD), a series of novel quinazolinone and vanillin cyanoacetamide based acrylamide derivatives (9a-z) were de...

  鉴于多靶点定向配体（MTDL）方法治疗阿尔茨海默病（AD），一系列新型喹唑啉酮和香草醛氰基乙酰胺基丙烯酰胺衍生物（9a-z）被开发出来。
• 具有AXL抑制活性的取代三唑化合物
  申请人：[en]NANJING CHIA TAI TIANQING PHARMACEUTICAL CO., LTD.;[zh]南京正大天晴制药有限公司

  公开号：WO2024051667A1

  公开（公告）日：2024-03-14

  公开了式（I）所示的具有AXL抑制活性的取代三唑化合物，其用于治疗和/或预防AXL受体酪氨酸激酶诱发的病症。
• Synthesis and Docking Study of Novel Pyranocoumarin Derivatives
  作者：S. Durga Karteek、A. Gopi Reddy、M. Bhuvan Tej、M. V. Basaveswara Rao

  DOI：10.1134/s1070428021020196

  日期：2021.2
• Derivatives of the N-(pyrid-2-yl)amides of 3-aminocrotonic acid as chelating ligands
  作者：V. A. Dorokhov、S. V. Baranin、A. Dib、K. L. Cherkasova、M. N. Bochkareva、V. S. Bogdanov

  DOI：10.1007/bf01150906

  日期：1992.4

  New chelating ligands, N-(pyrid-2-yl)amides of 4,4,4-trichloro-3-amino-2-cyanocrotonic acid have been synthesized from N-(pyrid-2-yl)amides of cyanoacetic acid and CCl3CN. It has been demonstrated that by the action of butylthiodibutylborane they form binuclear boron chelate complexes. Analogous chelates have also been obtained from the N-(pyrid-2-yl)amides of acetoacetic and 4,4,4-trichloro-3-aminocrotonic acids.
• DOROXOV, V. A.;BARANIN, S. V.;DIB, A.;BOGDANOV, V. S.;YAKOVLEV, I. P.;STA+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2107-2113
  作者：DOROXOV, V. A.、BARANIN, S. V.、DIB, A.、BOGDANOV, V. S.、YAKOVLEV, I. P.、STA+

  DOI：——

  日期：——