2-(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)acetonitrile | 37673-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)acetonitrile
• 英文别名: (3,4-dimethoxy-phenyl)-piperidin-1-yl-acetonitrile；<3.4-Dimethoxy-phenyl>-piperidino-essigsaeure-nitril；(3,4-Dimethoxyphenyl)(piperidin-1-yl)acetonitrile；2-(3,4-dimethoxyphenyl)-2-piperidin-1-ylacetonitrile
• CAS: 37673-07-7
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: FQELSXKYURXBIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)acetonitrile 、 3-phenylpropyl-magnesium bromide 在 乙醚 作用下， 生成 1-[1-(3,4-dimethoxy-phenyl)-4-phenyl-butyl]-piperidine
  参考文献：
  名称：

  DE963424

  摘要：

  公开号：
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酰氯 在 三乙胺 、 molybdenum hexacarbonyl 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 2-(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)acetonitrile
  参考文献：
  名称：

  Mo（CO）6催化的羧酰胺还原官能团直接合成α-氨基腈

  摘要：

  Mo（CO）6催化将酰胺选择性还原成中间体半胱氨酸再加上廉价且易于操作的TMDS（1,1,3,3-四甲基二硅氧烷）作为还原剂，随后用氰化物源捕获半胱氨酸，可以直接合成α-氨基腈。此处介绍的方法显示出高水平的化学选择性，可以在存在官能团（例如酮，亚胺，醛和酸）的情况下还原酰胺，这为广泛范围内的α-氨基腈的合成提供了一条简单途径高产量的功能。此外，该方法的适用性通过扩大规模的实验以及将目标化合物衍生为可合成的有趣产品来证明。

  DOI：

  10.1002/anie.201807735

文献信息

• Reactions of carbanions from 2-(dialkylamino)-arylacetonitriles with acetylene - simple syntheses of 1,3-dienamines and 1,4-diketones1
  作者：Andrzej Jończyk、Dariusz Lipiak、Tadeusz Zdrojewski

  DOI：10.1016/s0040-4020(01)81381-8

  日期：1990.1

  reacts with acetylene (2) in the presence of solid sodium hydroxide and tetrabutylammonium bromide (TBABr) as a catalyst, in DMSO, to give the vinyl derivative 3a. Whereas aminonitriles 1b-i, in the reaction with 2, afford dienamines 7. The different reactivity of 1a as compared to 1b-i is explained in terms of the different basicity of the amino moiety in vinyl derivatives 3. Dienamines 7 were hydrolyzed

  已经发现吗啉腈1a在固体氢氧化钠和四丁基溴化铵（TBABr）作为催化剂存在下，在DMSO中与乙炔（2）反应，得到乙烯基衍生物3a。而氨基腈1b-i在与2的反应中提供二烯胺7。用乙烯基衍生物3中氨基部分的不同碱性解释了1a与1b-i不同的反应性。将二烯胺7以高产率水解为1，4-二芳基丁丹-1，4-二酮8。
• Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever
  作者：Aurora L. Carreño Otero、Leonor Y. Vargas Méndez、Jonny E. Duque L.、Vladimir V. Kouznetsov

  DOI：10.1016/j.ejmech.2014.03.067

  日期：2014.5

  Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like alpha-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained alpha-aminonitriles could be considered as AChEIs with micromolar IC50 values ranging from 42.0 to 478.0 mu M (10.3-124.0 mu g/mL). Among this series, the best AChE inhibitor was the Pyrrolidine alpha-aminonitrile 3 (IC50 = 42 mu M) followed by the piperidine alpha-aminonitriles 2 and 6 (IC50 = 45 mu M and IC50 = 51 mu M, respectively), and the compound 7 (IC50 = 51 mu M). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides. (C) 2014 Elsevier Masson SAS. All rights reserved.
• JONCZYK, ANDRZEJ;LIPIAK, DARIUSZ;ZDROJEWSKI, TADEUSZ, TETRAHEDRON, 46,(1990) N, C. 1025-1038
  作者：JONCZYK, ANDRZEJ、LIPIAK, DARIUSZ、ZDROJEWSKI, TADEUSZ

  DOI：——

  日期：——