ethyl benzyl(oct-1-yn-1-yl)carbamate | 867157-12-8

• 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: ethyl benzyl(oct-1-yn-1-yl)carbamate
• 英文别名: ethyl N-benzyl-N-oct-1-ynylcarbamate
• CAS: 867157-12-8
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: ABCARFBCRGZCSA-UHFFFAOYSA-N

物化性质

• 沸点：
  389.4±35.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl benzyl(oct-1-yn-1-yl)carbamate 、 ethyl Phenylphosphinate 在 三苯基膦 、 nickel dibromide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以99%的产率得到ethyl (E)-benzyl(2-(ethoxy(phenyl)phosphoryl)oct-1-en-1-yl)carbamate
  参考文献：
  名称：

  Nickel-catalyzed regio- and stereoselective hydrophosphinylation of internal ynamides with H-phosphinates

  摘要：

  A method for the catalytic hydrophosphinylation of internal ynamides with H-phosphinates has been developed for the first time. The protocol employing the catalyst generated from NiBr2 and PPh3 could be applied to several types of ynamides and H-phosphinates, affording (E)-beta-aminovinylphosphinates in a highly regio- and stereoselective manner. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.10.042
• 作为产物：
  描述：

  1-iodooct-1-yne 、 N-苄基氨基甲酸乙酯 在 吡啶 、 双(三甲基硅烷基)氨基钾 、 copper(l) iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.17h， 以37%的产率得到ethyl benzyl(oct-1-yn-1-yl)carbamate
  参考文献：
  名称：

  Nickel-catalyzed regio- and stereoselective hydrophosphinylation of internal ynamides with H-phosphinates

  摘要：

  A method for the catalytic hydrophosphinylation of internal ynamides with H-phosphinates has been developed for the first time. The protocol employing the catalyst generated from NiBr2 and PPh3 could be applied to several types of ynamides and H-phosphinates, affording (E)-beta-aminovinylphosphinates in a highly regio- and stereoselective manner. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.10.042

文献信息

• Gold and Palladium Mediated Bimetallic Catalysis: Mechanistic Investigation through the Isolation of the Organogold(I) Intermediates
  作者：Arno Verlee、Thomas Heugebaert、Tom van der Meer、Pavel Kerchev、Kristof Van Hecke、Frank Van Breusegem、Christian V. Stevens

  DOI：10.1021/acscatal.9b02275

  日期：2019.9.6

  catalytic systems are a unique couple due to the carbophilic Lewis acidity of Au and the redox properties of Pd. To gain more insight into this bimetallic couple, a synthetic and mechanistic investigation was conducted. As key substrates, ynamides (N-alkynyl allyloxycarbamates and N-alkynyl ethyloxycarbamates) were used. Essential for the mechanistic part was the isolation of the organogold(I) intermediate

  基于Au-Pd的催化系统是独特的一对，这归因于Au的嗜碳路易斯酸度和Pd的氧化还原特性。为了深入了解这对双金属材料，进行了合成和机械研究。作为关键底物，使用乙酰胺（N-炔基烯丙氧基氨基甲酸酯和N-炔基乙氧基氨基甲酸酯）。机械部分必不可少的是有机金（I）中间体的分离，以验证所提出的机理。总共合成了18个多取代的恶唑酮和12个有机金（I）配合物。
• Regio- and stereoselective carbometallation reactions of <i>N</i>-alkynylamides and sulfonamides
  作者：Yury Minko、Morgane Pasco、Helena Chechik、Ilan Marek

  DOI：10.3762/bjoc.9.57

  日期：——

  The carbocupration reactions of heterosubstituted alkynes allow the regio- and stereoselective formation of vinyl organometallic species. N-Alkynylamides (ynamides) are particularly useful substrates for the highly regioselective carbocupration reaction, as they lead to the stereodefined formation of vinylcopper species geminated to the amide moiety. The latter species are involved in numerous synthetically useful transformations leading to valuable building blocks in organic synthesis. Here we describe in full the results of our studies related to the carbometallation reactions of N-alkynylamides.

  杂原子取代的炔烃的碳基化反应可以选择性地形成乙烯有机金属物种。尤其是N-炔基酰胺（ynamides）是高度选择性的碳基化反应的有用底物，因为它们导致与酰胺基团相结合的立体定义的乙烯铜物种的形成。后者参与许多合成有用的转化，导致有机合成中有价值的构建块的形成。在这里，我们全面描述了与N-炔基酰胺相关的碳金属化反应的研究结果。