tert-butyl N-cyclohexyl-N-(2-phenylethynyl)carbamate | 1383533-61-6

• 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-cyclohexyl-N-(2-phenylethynyl)carbamate
• CAS: 1383533-61-6
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: OZRIQWLFCIYQHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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-cyclohexyl-N-(2-phenylethynyl)carbamate 在 copper(l) chloride 作用下， 以 甲苯 为溶剂， 以73%的产率得到3-cyclohexyl-5-phenyloxazol-2(3H)-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。
• 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.
• 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。