N-甲基-N-(3-氰基丙基)苄胺 | 89690-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-甲基-N-(3-氰基丙基)苄胺
• 英文名称: N-methyl-N-(3-cyanopropyl)benzylamine
• 英文别名: 4-(benzylmethylamino)butyronitrile；4-(benzyl-methyl-amino)-butyronitrile；4-(Benzyl-methyl-amino)-butyronitril；4-[Benzyl(methyl)amino]butanenitrile
• CAS: 89690-05-1
• 化学式: C₁₂H₁₆N₂
• mdl: MFCD09753641
• 分子量: 188.272
• InChiKey: PFJZKEXLJVDQOP-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(3-氰基丙基)苄胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(1-苄基-1-甲基氨基)丁基胺
  参考文献：
  名称：

  Design, synthesis and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase

  摘要：

  Acetylcholinesterase inhibitors (AChEIs) are currently the drugs of choice, although only symptomatic and palliative, for the treatment of Alzheimer's disease (AD). Donepezil is one of most used AChEIs in AD therapy, acting as a dual binding site, reversible inhibitor of AChE with high selectivity over butyrylcholinesterase (BChE). Through a combined target-and ligand-based approach, a series of coumarin alkylamines matching the structural determinants of donepezil were designed and prepared. 6,7-Dimethoxycoumarin derivatives carrying a protonatable benzylamino group, linked to position 3 by suitable linkers, exhibited fairly good AChE inhibitory activity and a high selectivity over BChE. The inhibitory potency was strongly influenced by the length and shape of the spacer and by the methoxy substituents on the coumarin scaffold. The inhibition mechanism, assessed for the most active compound 13 (IC50 7.6 nM) resulted in a mixed-type, thus confirming its binding at both the catalytic and peripheral binding sites of AChE. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.045
• 作为产物：
  描述：

  苯亚甲基甲胺 在 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 20.0h， 生成 N-甲基-N-(3-氰基丙基)苄胺
  参考文献：
  名称：

  Concerning the synthesis of N-methylputrescine and its homologs

  摘要：

  DOI：

  10.1021/jo00185a040

文献信息

• POLYMERS FUNCTIONALIZED WITH NITRILE COMPOUNDS COMTAINING A PROTECTED AMINO GROUP
  申请人：Luo Steven

  公开号：US20120059112A1

  公开（公告）日：2012-03-08

  A method for preparing a functionalized polymer, the method comprising the steps of (i) polymerizing monomer with a coordination catalyst to form a reactive polymer; and (ii) reacting the reactive polymer with a nitrile compound containing a protected amino group.

  一种制备功能化聚合物的方法，包括以下步骤：(i)使用配位催化剂聚合单体以形成反应性聚合物；(ii)将反应性聚合物与含有受保护氨基团的腈化合物反应。
• POLYMERS FUNCTIONALIZED WITH NITRILE COMPOUNDS CONTAINING A PROTECTED AMINO GROUP
  申请人：Luo Steven

  公开号：US20120296041A1

  公开（公告）日：2012-11-22

  A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomer with an anionic initiator to form a reactive polymer; and (ii) reacting the reactive polymer with a nitrile compound containing a protected amino group, where the protected amino group is directly attached to a moiety selected from the group consisting of acyclic moieties, heterocyclic moieties, and non-aromatic cyclic moieties.

  一种制备功能化聚合物的方法，包括以下步骤：(i)使用阴离子引发剂聚合单体，形成反应性聚合物；(ii)将反应性聚合物与含有受保护氨基基团的腈化合物反应，其中受保护氨基基团直接连接到从以下组中选择的基团：非芳香环状基团，杂环基团和非环状基团。
• Heteroatom-Directed Alkylcyanation of Alkynes
  作者：Yoshiaki Nakao、Akira Yada、Tamejiro Hiyama

  DOI：10.1021/ja1017078

  日期：2010.7.28

  Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.
• Stereoselective synthesis of (Z)-trifluoromethyl enamines and their Lewis acid-mediated conversion into (E)-isomers
  作者：Biao Jiang、Fangjiang Zhang、Wennan Xiong

  DOI：10.1016/s0040-4020(01)01157-7

  日期：2002.1

  (Z)-beta-Trifluoromethyl enamines were prepared in high yield stereoselectively by reaction of 2-bromo-3,3,3-trifluoropropene with N-alkyl toluenesulfonamides and potassium t-butoxide in one pot via Michael addition and elimination processes. The (Z)-beta-trifluoromethyl enamines could be converted to the corresponding thermodynamically stable (E)-isomers promoted by Lewis acid catalysts at room temperature or thermal isomerization. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US8344066B2
  申请人：——

  公开号：US8344066B2

  公开（公告）日：2013-01-01