N,N-二烯丙基氨基乙腈 | 72524-91-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-二烯丙基氨基乙腈
• 英文名称: (N,N-diallylamino)acetonitrile
• 英文别名: Diallylaminoacetonitrile；2-[bis(prop-2-enyl)amino]acetonitrile
• CAS: 72524-91-5
• 化学式: C₈H₁₂N₂
• mdl: MFCD00045620
• 分子量: 136.197
• InChiKey: BPSBOLPAIOXQPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.375
• 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,N-二烯丙基氨基乙腈 生成 N²-<(E)-2-Propenyliden>glycinnitril
  参考文献：
  名称：

  N-取代的亚氨基乙腈的闪蒸真空热解生成和紫外光电子能谱研究

  摘要：

  顺式和反式1-苄基和1-烯丙基-2-氰基-3-苯基ze丁啶（1a和1b）在470°C的快速真空热解导致N-苄基和N-烯丙基亚氨基乙腈2a的E和Z异构体和图2b分别少量产品的旁图3a和3b中它们的[1,3]的质子移位。研究发现，氮杂环丁烷环的热断裂是通过C2-C3和C4-N键的裂解而完全区域选择性地发生的，而不是N-C2和C3-C4键的裂解。化合物的紫外光电子光谱借助于电离能的量子化学计算来测量和分析图2b。最简单的碳-氮双键在α，β取代时对电子结构的强烈修饰是由于腈基的吸电子作用和烯丙基的供体作用共同作用。

  DOI：

  10.1016/j.tet.2009.09.008
• 作为产物：
  描述：

  (N-allylamino)acetonitrile 、 3-溴丙烯 在 三乙胺 作用下， 以70%的产率得到N,N-二烯丙基氨基乙腈
  参考文献：
  名称：

  Gas phase thermolysis of allyl cyanomethyl amine, diallyl cyanomethyl amine, diethyl cyanomethyl amine, and diethyl propargyl amine

  摘要：

  AbstractThe title amines were pyrolyzed in a stirred‐flow reactor at 380–510°C, pressures of 8–15 torr and residence times of 0.3–2.4 s, using toluene as carrier gas. The substrates with an allyl group yielded propene and iminonitriles as reaction products. HCN is formed by decomposition of the iminonitriles. The first‐order rate coefficients for propene formation fit the Arrhenius equations Allyl cyanomethyl amine: Diallyl cyanomethyl amine: Diethyl cyanomethyl amine gave a 20:1 gas mixture of ehylene and ethane, plus HCN. The liquid product fraction contained mainly N‐ethyl methanaldimine. The first‐order rate coefficients for ethylene formation followed the Arrhenius equation Diethyl propargyl amine decomposed cleanly into allene and N‐ethyl ethanaldimine. The first‐order rate coefficients for allene formation fit the Arrhenius equation The results suggest that the above allyl and propargyl amines decompose unimolecularly by mechanisms involving six‐center cyclic transition states. For diethyl cyanomethyl amine, a nonchain free radical mechanism is proposed. © 1995 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550270203

文献信息

• FUSED RING HETEROCYCLE KINASE MODULATORS
  申请人：Chen Chixu

  公开号：US20080261921A1

  公开（公告）日：2008-10-23

  The present invention provides fused ring heterocycles as kinase modulators, pharmaceutical compositions containing these modulators, and methods of using these modulators to treat diseases mediated by kinase activity.

  本发明提供了融合环杂环化合物作为激酶调节剂，含有这些调节剂的药物组合物，以及使用这些调节剂治疗由激酶活性介导的疾病的方法。
• Titanium-mediated synthesis of bicyclic cyclopropylamines from unsaturated nitriles
  作者：Christophe Laroche、Philippe Bertus、Jan Szymoniak

  DOI：10.1016/s0040-4039(03)00325-3

  日期：2003.3

  Here we report an easy synthesis of bicyclic primary cyclopropylamines directly from unsaturated nitriles. The described reaction involves Ti(II)-mediated intramolecular coupling of alkene and nitrile moieties.

  在这里我们报道了直接从不饱和腈直接合成双环伯环丙胺的简单方法。所述反应涉及Ti（II）介导的烯烃和腈部分的分子内偶联。
• Ammonium nitriles and the use thereof as hydrophobic bleaching activators
  申请人：——

  公开号：US20040266644A1

  公开（公告）日：2004-12-30

  The invention relates to ammonium nitriles of general formula (I), wherein the radicals R 3 , R 4 , R 5 and X have the meaning as cited in the description and R 1 and R 2 respectively represent individually a straight or branched chained C 5 -C 24 -alkyl, alkenyl or alkylether group. The inventive compounds are used as bleaching activators in washing, cleaning, and disinfective agents and in textile and paper bleaching.

  本发明涉及通式(I)的氨基腈，其中基团R3、R4、R5和X的含义如描述中所述，而R1和R2分别代表直链或支链的C5-C24烷基、烯基或烷基醚基。这些新化合物可用作洗涤、清洁和消毒剂以及纺织品和纸张漂白剂中的漂白活性剂。
• Ag-Catalyzed Cyanomethylation of Amines Using Nitromethane as a C₁ Source
  作者：Takuya Takashima、Hamdiye Ece、Taiga Yurino、Takeshi Ohkuma

  DOI：10.1021/acs.orglett.3c02256

  日期：2023.8.18

  A new methodology to afford α-amino nitriles through oxidative cyanomethylation of amines using nitromethane as the methylene source in the presence of Me3SiCN without the addition of an external oxidant was developed. A catalytic amount of AgCN and a stoichiometric amount of LiBF4 cooperatively promoted the transformation. A wide variety of the amines, including both aromatic compounds and aliphatic

  开发了一种在 Me 3 SiCN存在下，在不添加外部氧化剂的情况下，使用硝基甲烷作为亚甲基源，通过胺的氧化氰甲基化来提供 α-氨基腈的新方法。催化量的AgCN和化学计量量的LiBF 4协同促进转化。多种胺，包括芳香族化合物和脂肪族胺，在氧化条件下不稳定，适用于该反应。
• Electrochemically enabled decyanative C(sp³)–H oxygenation of <i>N</i>-cyanomethylamines to formamides
  作者：Mu-Jia Luo、Wei Zhou、Ruchun Yang、Haixin Ding、Xian-Rong Song、Qiang Xiao

  DOI：10.1039/d3ob00313b

  日期：——

  Selective oxygenation of C(sp3)–H bonds adjacent to nitrogen atoms is a highly attractive strategy for synthesizing various formamide derivatives while preserving the substrate skeletons. Herein, an environmentally benign electrochemically enabled decyanative C(sp3)–H oxygenation of N-cyanomethylamines using H2O as a carbonyl oxygen atom source is described, leading to the synthesis of a large class

  与氮原子相邻的C(sp 3 )–H 键的选择性氧化是合成各种甲酰胺衍生物同时保留底物骨架的极具吸引力的策略。在此，描述了使用 H 2 O 作为羰基氧原子源对N-氰基甲胺进行环境友好的电化学脱氰 C(sp 3 )–H 氧化反应，从而以良好至优异的收率合成了一大类甲酰胺，具有在无金属和无氧化剂的条件下具有广泛的底物范围。这种电化学技术突出了将N-甲酰基轻松结合到一些重要的生物活性分子中。