2-(N-prop-2-ynylamino)acetonitrile | 56096-28-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N-prop-2-ynylamino)acetonitrile
• 英文别名: N-(2-Propynyl)aminoacetonitrile；N-propyne-2 aminoacetonitrile；2-(prop-2-ynylamino)acetonitrile
• CAS: 56096-28-7
• 化学式: C₅H₆N₂
• mdl: MFCD00137987
• 分子量: 94.116
• InChiKey: VKMQENXKRDPRHY-UHFFFAOYSA-N

物化性质

• 沸点：
  233.6±15.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(N-prop-2-ynylamino)acetonitrile 在 氢氧化钾 作用下， 300.0 ℃ 、0.13 Pa 条件下， 生成 N-methylidenepropadiene-1,2 amine
  参考文献：
  名称：

  快速真空热解α-氨基腈并随后在固体碱上去除HCN，这是反应性N-亚甲基胺的“一线”多步骤序列

  摘要：

  通过快速真空热解α-氨基腈并随后在固体碱上除去HCN，在低温下以冷凝状态分离出带有烷基或官能团的反应性亚甲基胺。

  DOI：

  10.1039/c39850000951
• 作为产物：
  描述：

  炔丙胺 、 溴乙腈 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以100%的产率得到2-(N-prop-2-ynylamino)acetonitrile
  参考文献：
  名称：

  Synthesis of 5,6,7,8-Tetrahydro-1,6-naphthyridines and Related Heterocycles by Cobalt-Catalyzed [2 + 2 + 2] Cyclizations

  摘要：

  Microwave-promoted, cobalt-catalyzed intramolecular [2 + 2 + 2] cyclizations of dialkynylnitriles successfully gave 5,6,7,8-tetrahydro-1,6-naphthyridines. The efficient synthesis of these relatively simple, yet rarely addressed heterocycles enabled the preparation of a collection of these compounds.

  DOI：

  10.1021/ol0625280

文献信息

• Studies on anti-Fusarium disease activity of aminonitrile derivatives. I. Preventive activities of N-substituted-.ALPHA.-aminonitriles against Fusarium diseases.
  作者：Osamu KIRINO、Hirofumi OSHITA、Tadashi OISHI、Toshiro KATO

  DOI：10.1271/bbb1961.44.25

  日期：——

  Forty nine N-substituted-α-aminonitriles were prepared and their preventive activities against Fusarium diseases were determined. Relationships between chemical structure and preventive activity were examined and the systemic movement in plants was investigated with 14C-N-allylaminoacetonitrile. Of the compounds tested, N-sec-butyl-α-aminoisobutyronitrile and N-allylaminoacetonitrile were most effective in controlling yellows of the Japanese radish which were caused by Fusarium oxvsporum f. sp. raphani. N-Allylaminoacetonitrile showed remarkable systemic movement and a potent preventive activity against Fusarium wilts of cucumber and tomato not only by the soil drench test but also by the foliar spray assay.

  制备了49种代N-取代-α-氨基腈，并测定了它们对镰刀菌病害的防治活性。研究了化学结构与防治活性之间的关系，并使用14C-N-烯丙基氨基乙腈研究了其在植物中的系统运动。在测试的化合物中，N-仲丁基-α-氨基异丁腈和N-烯丙基氨基乙腈对由尖孢镰刀菌萝卜专化型引起的日本萝卜黄化病具有最佳的防治效果。N-烯丙基氨基乙腈显示出卓越的系统运动，对黄瓜和番茄的镰刀菌萎蔫病不仅通过土壤浸渍测试，还通过叶面喷雾法表现出强效的预防活性。
• Flash vacuum thermolysis of α-aminonitriles and subsequent HCN removal on solid base, a ‘one line’ multistep sequence to reactive N-methyleneamines
  作者：J. C. Guillemin、J. M. Denis

  DOI：10.1039/c39850000951

  日期：——

  Reactive methyleneamines bearing alkyl or functional groups are isolated at low temperature in the condensate state by flash vacuum thermolysis of α-aminonitriles and subsequent vapour phase HCN removal on solid base.

  通过快速真空热解α-氨基腈并随后在固体碱上除去HCN，在低温下以冷凝状态分离出带有烷基或官能团的反应性亚甲基胺。
• Intramolecular Cyclization of Alkynylheteroaromatic Substrates Bearing a Tethered Cyano Group: A Strategy for Accessing Fused Pyridoheterocycles
  作者：Niklas Kraemer、Erin M. Eason、Thomas R. Hoye

  DOI：10.1021/acs.joc.3c01411

  日期：2023.9.1

  cyclize in an overall tetradehydro-Diels–Alder reaction to give products in which the initial heterocycle bears a newly fused pyridine ring. Base-promoted tautomerization of the alkyne to its isomeric allene allows this process to occur at ambient temperature. DFT studies support many of the mechanistic interpretations of the overall results.

  含有共轭炔烃和侧腈的杂环底物显示在整个四氢-狄尔斯-阿尔德反应中环化，得到初始杂环带有新稠合吡啶环的产物。碱促进的炔烃互变异构为其异构丙二烯，使得该过程可以在环境温度下发生。 DFT 研究支持总体结果的许多机械解释。
• Discovery of long-acting N-(cyanomethyl)-N-alkyl-l-prolinamide inhibitors of dipeptidyl peptidase IV
  作者：Takashi Kondo、Takahiro Nekado、Isamu Sugimoto、Kenya Ochi、Shigeyuki Takai、Atsushi Kinoshita、Akira Hatayama、Susumu Yamamoto、Kazuhito Kawabata、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2007.10.005

  日期：2008.1

  Details of structure-activity relationships (SAR) for P2 moiety of a P1 2-cyanopyrrolidine dipeptidyl peptidase IV (DPP-IV) inhibitor 4a including stereochemistry are presented. Based on this information, a series of PI (N-alkyl)aminoacetonitrile analogs 9-20 possessing optimal P2 structure were synthesized and evaluated as inhibitors of DPP-IV. Among them, a representative compound 11, N-(cyanomethyl)-N-ethyl-L-prolinamide, was further evaluated to determine its effect on the plasma glucose level. Also 4a, 10, and 11 were evaluated for their isozyme selectivity to predict their safety problems. (C) 2007 Elsevier Ltd. All rights reserved.
• FR2242374
  申请人：——

  公开号：——

  公开（公告）日：——