2-(piperidin-1-ylmethylene)malononitrile | 73541-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(piperidin-1-ylmethylene)malononitrile
• 英文别名: 2-piperidin-1-ylmethylenemalononitrile；piperidin-1-ylmethylene-malononitrile；Piperidinomethylen-malonsaeure-dinitril；Piperidinomethylen-malonsaeuredinitril；3-Piperidino-2-cyan-acrylnitril；Malononitrile, (piperidinomethylene)-；2-(piperidin-1-ylmethylidene)propanedinitrile
• CAS: 73541-92-1
• 化学式: C₉H₁₁N₃
• 分子量: 161.206
• InChiKey: IDMBBRCPKAVZMT-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solv: ethyl acetate (141-78-6); pentane (109-66-0))
• 沸点：
  270.5±33.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(piperidin-1-ylmethylene)malononitrile 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 9.0h， 以35%的产率得到2-piperidin-1-ylmethyl-propane-1,3-diamine trihydrochloride
  参考文献：
  名称：

  Hydrogenation of Imino‐bisnitriles—Synthesis of Novel Triamines

  摘要：

  DOI：

  10.1080/00397910601038970
• 作为产物：
  描述：

  哌啶 、 3-bromoisothiazole-4-carbonitrile 以 乙醇 为溶剂， 反应 24.0h， 以84%的产率得到2-(piperidin-1-ylmethylene)malononitrile
  参考文献：
  名称：

  Regioselective hydrodehalogenation of 3,5-dihaloisothiazole-4-carbonitriles: synthesis of 3-haloisothiazole-4-carbonitriles

  摘要：

  3,5-Dibromoisothiazole-4-carbonitrile 1 treated with Zn or In dust (5 equiv) and HCO2H undergoes regioselective hydrodebromination to give 3-bromoisothiazole-4-carbonitrile 3 in 70-74% yield. Similarly, 5-bromo and iodo 3-chloroisothiazole-4-carbonitriles 8 and 9 give 3-chloroisothiazole-4-carbonitrile 4 in 77 and 85% yields, respectively. Also hydrodeamination of 5-amino-3-chloroisothiazole-4-carbonitrile 7 using isoamyl nitrite gives the latter in 95% yield. The dibromoisothiazole 1 reacts with Zn dust in either DCO2D or HCO2D to give 3-bromo-5-deuterioisothiazole-4-carbonitrile 10 in 71 and 58% yields, respectively. The 3-bromoisothiazole 3 reacts with cyclic dialkylamines to give the corresponding 2-(dialkylaminomethylene)-malononitriles and not the expected 3-dialkylaminoisothiazole-4-carbonitriles. Finally, the 3-bromoisothiazole 3 is readily converted into both 3-bromoisothiazole-4-carboxamide 19 and the carboxylic acid 20. All products are fully characterized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.065

文献信息

• Kreutzberger; Kreutzberger, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 2, p. 232 - 234
  作者：Kreutzberger、Kreutzberger

  DOI：——

  日期：——
• 1,1′-Dicyano-2-substituted ethylenes: A new class of glucose uptake inhibitors in antifilarial chemotherapy
  作者：Swati Tewari、P.M.S. Chauhan、A.P. Bhaduri、S.N. Singh、Nigar Fatma、R.K. Chatterjee、V.M.L. Srivastava

  DOI：10.1016/s0960-894x(97)00322-3

  日期：1997.7

  Several 1,1'-dicyano-2-substituted ethylenes (2-16) were synthesized and evaluated for in vivo antifilarial activity. Some of the screened compounds showed significant antifilarial response against Acanthocheilonema viteae in rodents. (C) 1997 Elsevier Science Ltd.