N-(prop-2-en-1-yl)-N-(prop-2-yn-1-yl)benzamide | 119548-48-0

• 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: N-(prop-2-en-1-yl)-N-(prop-2-yn-1-yl)benzamide
• 英文别名: N-Allyl-N-benzoyl-N-prop-2-ynylamine；N-allyl-N-(prop-2-ynyl)benzamide；N-allyl-N-propargylbenzamide；4-benzylazahept-1-ene-6-yne；Benzamide, N-2-propenyl-N-2-propynyl-；N-prop-2-enyl-N-prop-2-ynylbenzamide
• CAS: 119548-48-0
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: WNQMTOLCVOWVJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(prop-2-en-1-yl)-N-(prop-2-yn-1-yl)benzamide 在 dicobalt octacarbonyl 、 silica gel 作用下， 生成 2-Benzoyl-hexahydro-cyclopenta[c]pyrrol-5-one
  参考文献：
  名称：

  固相Pauson-Khand反应的研究：选择性原位烯酮还原为3-氮杂双环[3.3.0]辛酮

  摘要：

  在没有氧的情况下，一系列N-保护的烯丙基炔丙基胺的Smit-Caple DSAC Pauson-Khand环化反应以极好的收率形成了饱和氮杂双环[3.3.0]辛酮。在空气中标准环化得到饱和和不饱和酮的混合物。

  DOI：

  10.1016/s0040-4039(00)60352-0
• 作为产物：
  描述：

  苯甲酰氯 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 37.0h， 生成 N-(prop-2-en-1-yl)-N-(prop-2-yn-1-yl)benzamide
  参考文献：
  名称：

  The visible-light-promoted intermolecular para-cycloadditions of allenamides on naphthalene

  摘要：

  DOI：

  10.1016/j.tchem.2023.100053

文献信息

• A Unique Ruthenium Carbyne Complex: A Highly Thermo-endurable Catalyst for Olefin Metathesis
  作者：Mingbo Shao、Lu Zheng、Weixia Qiao、Jingjing Wang、Jianhui Wang

  DOI：10.1002/adsc.201200119

  日期：2012.10.8

  A cationic ruthenium carbyne complex was prepared and was found to initiate olefin metathesis reactions with good activities, which throws a new light on the design of a new type of ruthenium catalyst for RCM reactions. More importantly, no double bond isomerized by-product was observed even at elevated temperatures in reactions catalyzed by the new carbyne complex. A mechanism involving the in situ

  制备了一种阳离子钌卡宾络合物，发现该催化剂能引发烯烃复分解反应，并具有良好的活性，这为新型的用于RCM反应的钌催化剂的设计提供了新的思路。更重要的是，即使在新的卡宾络合物催化的反应中，即使在升高的温度下，也没有观察到双键异构化的副产物。还提出了一种机制，该机制涉及通过将碘化物添加到卡宾碳上而将卡宾碳烯原位转化为钌卡宾络合物。
• Gold Catalysis: Products and Intermediates Obtained from N-Propargylcarboxamides Bearing Additional Substituents on Nitrogen
  作者：A. Stephen K. Hashmi、Lise Molinari、Frank Rominger、Thomas Oeser

  DOI：10.1002/ejoc.201100179

  日期：2011.4

  substrates with additional substituents on the nitrogen atom was investigated. Under aqueous conditions acyloxy-substituted allylammonium salts could selectively be obtained. Monitoring of the reactions by 1 H NMR spectroscopy indicated the presence of an intermediate. Then switching to anhydrous reaction conditions allowed the isolation and characterization of these intermediates, oxazoliniminium species

  研究了几种炔丙酰胺底物与氮原子上的额外取代基的反应。在水性条件下，可以选择性地获得酰氧基取代的烯丙基铵盐。通过 1 H NMR 光谱监测反应表明存在中间体。然后切换到无水反应条件允许分离和表征这些中间体，恶唑啉鎓物种。在碱性条件下处理烯丙基铵盐导致酰基从氧原子转移到氮原子，这证明这些产物不是仅通过金催化的三键直接水合形成的，同时很好地解释了两个三键中只有一个的选择性一水合。
• Rhodium (1) catalysed regiospecific cyclisation of 1,6-enynes to methylenecyclohex-2-enes
  作者：Ronald Grigg、Paul Stevenson、Tanachat Worakun

  DOI：10.1016/s0040-4020(01)86200-1

  日期：1988.1
• A six-coordinated cationic ruthenium carbyne complex with liable pyridine ligands: synthesis, structure, catalytic investigation, and DFT study on initiation mechanism
  作者：Guiyan Liu、Lu Zheng、Mingbo Shao、Huizhu Zhang、Weixia Qiao、Xiaojia Wang、Bowen Liu、Haitao Zhao、Jianhui Wang

  DOI：10.1016/j.tet.2014.05.060

  日期：2014.8

  A novel six-coordinated high-valence cationic ruthenium carbyne complex bearing two liable pyridine ligands was prepared in high yield by the reaction of the ruthenium-based complex (IMesH(2))(Cl)(2)(C5H5N)(2)Ru center dot CHPh [IMesH(2)=1,3-dimesityl-4,5-dihydroimida-zol-2-ylidene] with excess iodine as an oxidant in CH2Cl2 at 25 degrees C under N-2. The new ruthenium carbyne-based complex shows moderate to good catalytic activity for ring-closing metathesis reactions. Importantly, no double bond isomerization by-product was produced at elevated reaction temperatures (100 degrees C-137 degrees C) in the reaction catalyzed by the synthesized ruthenium carbyne complex. A mechanism involving the in situ conversion of the ruthenium carbyne through the addition of an iodide to the carbyne carbon was also proposed, and DFT calculations were performed to explain the initiating mechanism. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Cyclopropylpyrrolidines via Reaction of <i>N</i>-Allyl-<i>N</i>-propargylamides with a Molybdenum Carbene Complex. Effect of Substituents and Reaction Conditions
  作者：Daniel F. Harvey、Dina M. Sigano

  DOI：10.1021/jo9519930

  日期：1996.1.1

  Previous studies have demonstrated that group 6 carbene complexes react with alpha,omega-enynes to form vinylcyclopropane derivatives in good to excellent yield, and that the length and composition of the tether between the alkyne and the alkene often has a dramatic impact on the viability of this reaction pathway. The reactivity of allylpropargyl amine derivatives with pentacarbonyl(1-methoxypentylidene)molybdenum(0) (14a) was investigated in order to provide further insight into the steric and electronic factors controlling this reaction. Treatment of allylpropargyl amines with 14a failed to produce the desired cyclization products while treatment of allylpropargyl amides with 14a led to the expected cyclopropylpyrrolidine systems in good to excellent yields. Higher yields are obtained when the reaction is conducted in a sealed vial in the presence of atmospheric oxygen.