tert-butyl N-benzyl-N-[2-(4-chlorophenyl)ethynyl]carbamate | 1383533-46-7

• 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-benzyl-N-[2-(4-chlorophenyl)ethynyl]carbamate
• CAS: 1383533-46-7
• 化学式: C₂₀H₂₀ClNO₂
• 分子量: 341.837
• InChiKey: HDTQSQXSINUHEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  tert-butyl N-benzyl-N-[2-(4-chlorophenyl)ethynyl]carbamate 在 copper(l) chloride 作用下， 以 甲苯 为溶剂， 以84%的产率得到3-Benzyl-5-(4-chlorophenyl)-1,3-oxazol-2-one
  参考文献：
  名称：

  A Facile Access to 3,5-Disubstituted Oxazolones Featuring a Cu-catalyzed Cyclization of N-Alkynyl tert-Butyl Carbamates

  摘要：

  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。

  DOI：

  10.1246/cl.2012.636

文献信息

• Preparation of 3,4,5-Trisubstituted Oxazolones by Pd-Catalyzed Coupling of <i>N</i>-Alkynyl <i>tert</i>-Butyloxycarbamates with Aryl Halides and Related Electrophiles
  作者：Zenghui Lu、Weijian Cui、Siyuan Xia、Yihui Bai、Fang Luo、Gangguo Zhu

  DOI：10.1021/jo301794w

  日期：2012.11.2

  oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reaction provides a convenient access to diversely substituted oxazolones in satisfactory yields and shows good functional group compatibility.

  通过将N-炔基叔丁氧基氨基甲酸酯与芳基卤化物和相关的亲电试剂偶联，已经获得了一种新型的钯催化的3,4,5-三取代的恶唑酮组装方法，该方法涉及氧化加成，然后进行氧化钯/还原消除。该反应以令人满意的产率方便地获得了各种取代的恶唑酮，并显示出良好的官能团相容性。
• 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。
• 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.