benzyl(1-ethyl-1-methylprop-2-ynyl)amine | 138971-90-1

• 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: benzyl(1-ethyl-1-methylprop-2-ynyl)amine
• 英文别名: N-benzyl-3-methylpent-1-yn-3-amine
• CAS: 138971-90-1
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: HBEKCQCDDAETBV-UHFFFAOYSA-N

物化性质

• 沸点：
  284.3±15.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzyl(1-ethyl-1-methylprop-2-ynyl)amine 在 palladium diacetate 2,6-二叔丁基-4-甲基吡啶 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-benzyl-4-(2-chlorobenzyl)-5-ethyl-5-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  一种合成高度取代的 3-吡咯啉-2-酮的新方法

  摘要：

  在碳酸盐碱存在下，在室温或 80 °C 下，碱促进的内部 N-炔丙基-丙二酰胺环化以良好的收率提供了高度取代的 3-吡咯啉-2-酮。

  DOI：

  10.1055/s-2006-942393
• 作为产物：
  描述：

  3-甲基-1-戊炔-3-醇 在 magnesium(II) perchlorate 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 benzyl(1-ethyl-1-methylprop-2-ynyl)amine
  参考文献：
  名称：

  An Unprecedented Pd-Catalyzed, Water-Promoted Sequential Oxidative Aminocarbonylation−Cyclocarbonylation Process Leading to 2-Oxazolidinones

  摘要：

  An unprecedented, PdI2-catalyzed, sequential oxidative aminocarbonylation-cyclocarbonylation process, leading to 2-oxazolidinone derivatives 3 in good to excellent yields starting from readily available alpha,alpha-disubstituted 2-ynylamines 1 and secondary amines 2, is reported. In the case of an alpha-monosubstituted substrate, the initially formed 2-oxazolidinone derivative underwent shift of the double bond to give a 3H-oxazol-2-one derivative in excellent isolated yield.

  DOI：

  10.1021/ol071332c

文献信息

• The Reaction of Acetylenic Amines with Tetraethylammonium Carbonate and Hydrogen Carbonate; Synthesis of 5-Methylene-1,3-oxazolidin-2-ones
  作者：Leucio Rossi、Antonio Arcadi、Achille Inesi、Fabio Marinelli、Mirella Verdecchia

  DOI：10.1055/s-2004-836036

  日期：——

  The reaction of acetylenic amines 1 with electrochemically generated tetraethylammonium carbonate (TEAC) or chemically generated tetraethylammonium hydrogen carbonate (TEAHC) is reported. Unsubstituted or substituted 5-methylene-1,3-oxazolidin-2-ones 2 are obtained in moderate to very high yields according to the reaction conditions adopted and to the nature of the substrate.

  报道了炔胺 1 与电化学生成的四乙基碳酸铵 (TEAC) 或化学生成的四乙基碳酸氢铵 (TEAHC) 的反应。根据所采用的反应条件和底物的性质，以中等至非常高的产率获得未取代或取代的5-亚甲基-1，3-恶唑烷-2-酮2。
• Electrochemically Promoted C−N Bond Formation from Acetylenic Amines and CO₂. Synthesis of 5-Methylene-1,3-oxazolidin-2-ones
  作者：Marta Feroci、Monica Orsini、Giovanni Sotgiu、Leucio Rossi、Achille Inesi

  DOI：10.1021/jo0511804

  日期：2005.9.1

  An efficient electrochemical synthesis of 5-methylene-1,3-oxazolidin-2-ones (2a−h) from acetylenic amines (1a−h) and carbon dioxide has been achieved by direct electrolysis of solution of MeCN and Et4NPF6 containing the amine, with subsequent CO2 bubbling and heating. The yields vary from good to excellent, the conditions are mild, and the use of toxic and harmful chemicals and catalysts is avoided

  的5-亚甲基-1,3-恶唑烷-2-酮（一种有效的电化学合成2A - ħ从炔胺（）1A - H ^）和二氧化碳已经通过的MeCN和Et的溶液直接电解来实现4 NPF 6含有胺，随后鼓入CO 2并加热。收率各有不同，条件温和，避免使用有毒有害的化学物质和催化剂。
• Copper/DTBP-Promoted Oxyselenation of Propargylic Amines with Diselenides and CO₂: Synthesis of Selenyl 2-Oxazolidinones
  作者：Jia-Min Chen、Lin Qi、Linlin Zhang、Li-Jun Li、Cong-Ying Hou、Wei Li、Li-Jing Wang

  DOI：10.1021/acs.joc.0c01519

  日期：2020.8.21

  A highly efficient electrophilic oxyselenation of propargylic amines with diselenides and CO2 under atmospheric pressure promoted by copper/DTBP is reported. Various biologically important selenyl 2-oxazolidinones were produced in moderate to excellent yields. The developed method features a broad substrate scope, easy scalability, and mild reaction conditions.

  据报道，在大气压下，铜/ DTBP促进了炔丙基胺与二硒化物和CO 2的高效亲电氧硒化反应。以中等至优异的产率生产了各种生物学上重要的硒烯基2-恶唑烷酮。所开发的方法具有广泛的底物范围，易于扩展和反应条件温和的特点。
• Silylformylation–desilylation of propargyl amides: synthesis of α,β-unsaturated aldehydes
  作者：Laura Antonella Aronica、Patrizio Raffa、Giulia Valentini、Anna Maria Caporusso、Piero Salvadori

  DOI：10.1016/j.tetlet.2005.11.054

  日期：2006.1

  α,β-Unsaturated aldehydes are prepared from easily available propargyl amides through a two-step sequence of silylformylation–desilylation reactions. The substituent on the nitrogen atom markedly influences both reactions, β-silylalkenals being formed in the presence of tosyl or tert-butoxycarbonyl protected amines. TBAF is employed to induce the desilylation process that is performed under very mild

  α，β-不饱和醛是由容易获得的炔丙基酰胺通过两步的甲硅烷基甲酰化-去甲硅烷基化反应制得的。氮原子上的取代基显着影响两个反应，在甲苯磺酰基或叔丁氧羰基保护的胺存在下会形成β-甲硅烷基烯醛。TBAF用于诱导在非常温和的实验条件下进行的脱甲硅烷基化过程。当甲苯磺酰胺醛反应生成2-甲基芳基-2-烯醛时，发生了当代的消除步骤，同时可以抑制该过程，将官能团改变为NBOC，从而形成β-氨基羰基化合物。
• Versatile synthesis of beta-lactams, gamma-lactams or oxalines by palladium-catalysed oxidative carbonylation of 1-substituted prop-2-ynylamines
  作者：Alex Bonardi、Mirco Costa、Bartolo Gabriele、Giuseppe Salerno、Gian Paolo Chiusoli

  DOI：10.1016/0040-4039(95)01514-0

  日期：1995.10

  alfa-Methylene-beta-lactams possessing a Z-alkoxycarbonyl group are formed directly from the reaction of N-alkyl-substituted prop-2-ynylamines with CO, air and alcohols, under the catalytic action of palladium on carbon in conjunction with potassium iodide, while gamma-lactams or oxazolines are obtained with unsubstituted or acylated amines.

  阿尔法亚甲基的β内酰胺结合具有一Z-烷氧基羰基是直接从N-烷基-取代的丙-2- ynylamines用CO，空气和醇的反应形成，钯碳催化作用下与碘化钾，而γ-内酰胺或恶唑啉是通过未取代或酰化的胺获得的。