tert-butyl N-butyl-N-(2-phenylethynyl)carbamate | 1383533-60-5

• 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: tert-butyl N-butyl-N-(2-phenylethynyl)carbamate
• CAS: 1383533-60-5
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: LFFVTIHEPBLFMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-butyl-N-(2-phenylethynyl)carbamate 在 四(三苯基膦)钯 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以53%的产率得到4-bromo-3-butyl-5-phenyl-3H-oxazol-2-one
  参考文献：
  名称：

  钯催化的酰胺类分子内环化反应：4-卤代恶唑酮的合成

  摘要：

  开发了一种温和有效的方法，该方法涉及Pd（PPh 3）4催化的N-炔基烷氧基氨基甲酸酯与CuCl 2或CuBr 2的分子内环化反应，用于合成4-卤代恶唑酮。该反应显示出良好的功能耐受性，为4-卤代恶唑酮提供了新的，有效的和快速的合成方法。所得的4-卤代恶唑酮可通过Pd催化的交叉偶联反应作为3,4,5-三取代的恶唑酮的潜在潜在前体。

  DOI：

  10.1021/acs.joc.5b00071

文献信息

• Generation of Oxazolidine-2,4-diones Bearing Sulfur-Substituted Quaternary Carbon Atoms by Oxothiolation/Cyclization of Ynamides
  作者：Hai Huang、Junzhen Fan、Guangke He、Zhimin Yang、Xiaodong Jin、Qi Liu、Hongjun Zhu

  DOI：10.1002/chem.201504356

  日期：2016.2.12

  A novel method for metal‐free oxothiolation of ynamides to construct oxazolidine‐2,4‐diones bearing sulfur‐substituted quaternary carbon atoms has been developed. It represents a rare C−O bond cleavage of ynamides, as well as a facile and tandem approach for the formation of C−O, C−S, and C−Cl bonds. This redox‐neutral protocol can be applied to the synthesis of multisubstituted oxazolidine‐2,4‐diones

  开发了一种新型的无金属羰基硫代酰胺化方法，以构建带有硫取代的季碳原子的恶唑烷-2,4-二酮。它代表了罕见的炔酰胺的C-O键断裂，以及形成C-O，C-S和C-Cl键的便捷串联方法。该氧化还原中性方案可用于在温和条件下以良好的化学选择性和分离产物的高产率合成多取代的恶唑烷-2,4-二酮。
• PhI(OAc)₂-mediated trifluoromethylthiolation/oxidative cyclization of ynamides
  作者：Shixuan Su、Zhipeng Yan、Xingyuan Ye、Jingyang Wang、Yuan Li、Guangke He

  DOI：10.1039/d1ob01642c

  日期：——

  A PhI(OAc)2-mediated trifluoromethylthiolation/oxidative cyclization of ynamides with the Shen reagent has been established herein, providing a facile access to CF3S-substituted oxazolidine-2,4-diones bearing a quaternary carbon center in 38–85% yields with chemoselectivities of up to 99/1.

  本文建立了PhI(OAc) 2介导的炔酰胺与Shen 试剂的三氟甲基硫醇化/氧化环化，提供了一种容易获得具有38-85% 季碳中心的CF 3 S-取代的恶唑烷-2,4-二酮的途径产率高达 99/1 的化学选择性。
• A Facile Access to 3,5-Disubstituted Oxazolones Featuring a Cu-catalyzed Cyclization of <i>N</i>-Alkynyl <i>tert</i>-Butyl Carbamates
  作者：Zenghui Lu、Zhaozhen Yang、Weijian Cui、Gangguo Zhu

  DOI：10.1246/cl.2012.636

  日期：2012.6.5

  Using cheap and readily accessible CuCl as the catalyst, an operationally simple and efficient method for the synthesis of 3,5-disubstituted oxazolones has been realized by the cyclization of N-alkynyl tert-butyl carbamates. The reaction proceeds under mild reaction conditions and shows good functional group compatibility.

  利用廉价且容易获得的 CuCl 作为催化剂，通过 N-炔基叔丁基氨基甲酸环化，实现了一种操作简单且高效的 3,5 二甲基噁唑酮合成方法。该反应在温和的反应条件下进行，并显示出良好的官能团兼容性。
• Approach to highly functionalized oxazolones by a Pd-catalyzed cyclization of N-alkynyl tert-butyloxycarbamates
  作者：Zenghui Lu、Xiaowei Xu、Zhaozhen Yang、Lichun Kong、Gangguo Zhu

  DOI：10.1016/j.tetlet.2012.04.074

  日期：2012.7

  A mild and operationally simple approach to highly functionalized oxazolones has been developed, which involves an intramolecular oxypalladation of N-alkynyl tert-butyloxycarbamates, followed by either protonolysis of the alkenyl C-Pd bond to afford 3,5-disubstituted oxazolones or allylation with allyl halides in the presence of Ag2CO3 to generate 3,4,5-trisubstituted oxazolones, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
• Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective Iodocyclization of Ynamides
  作者：Hai Huang、Xiaolin Zhu、Guangke He、Qi Liu、Junzhen Fan、Hongjun Zhu

  DOI：10.1021/acs.orglett.5b01045

  日期：2015.5.15

  Two efficient processes based on the iodocyclization of ynamides have been developed: (i) N-alkynyl tert-butyloxycarbamates were found to undergo a rare 6-exo-dig ring closure reaction affording 1,3,5-oxadiazin-2-ones by using acetonitrile as solvent; (ii) In the absence of acetonitrile, N-alkynyl tert-butyloxycarbamates could undergo 5-endo-dig cyclization providing oxazolones.