(4-chlorophenyl)-phenylethynyl-carbamic acid tert-butyl ester | 1011269-15-0

• 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: (4-chlorophenyl)-phenylethynyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(4-chlorophenyl)-N-(2-phenylethynyl)carbamate
• CAS: 1011269-15-0
• 化学式: C₁₉H₁₈ClNO₂
• 分子量: 327.81
• InChiKey: CMEWUKKVMRJXBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (4-chlorophenyl)-phenylethynyl-carbamic acid tert-butyl ester 在 silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以99%的产率得到3-(4-chlorophenyl)-5-phenyl-oxazol-2-one
  参考文献：
  名称：

  An Efficient Silver Tetrafluoroborate-Catalyzed Cycloisomerization of Ynamides

  摘要：

  DOI：

  10.3987/com-18-s(f)21
• 作为产物：
  描述：

  4-氯-(N-Boc)苯胺 、 苯基溴乙炔 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 (4-chlorophenyl)-phenylethynyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  酰胺的无金属水合：酰胺的便捷方法

  摘要：

  开发了三氟乙酸（TFA）介导的酰胺水合反应，这是合成N-单取代酰胺的有效方法。这种方便的方法在室温条件下对各种各样的基材都有效，并且通过简单的后处理工艺可以高到极好的收率获得产品。

  DOI：

  10.1016/j.tetlet.2016.03.052

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。
• 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。
• Cu(I)‐Catalyzed Oxytrifluoromethylation of <i>N</i> ‐Boc‐Ynamides for the Construction of Trifluoromethylated Oxazolones
  作者：Yue Zuo、Xingyuan Ye、Dongjie Jiang、Shuai Zhou、Mengyuan Yu、Guangke He

  DOI：10.1002/adsc.202200971

  日期：2022.12.8

  A chemo-selective copper(I)-catalyzed oxytrifluoromethylation of N-Boc-ynamides with TMSCF3 has been achieved, affording the trifluoromethylated oxazolones in 51–99% yields. The reaction proceeds at room temperature and tolerates a variety of functional groups such as −X, −OMe, alkenyl, and other substituents. The resulting oxazolones provide access to α-CF3-substituted amines through decarboxylative

  已经实现了化学选择性铜 (I) 催化的N -Boc-ynamides 与 TMSCF 3的氧三氟甲基化，以 51-99% 的收率提供三氟甲基化恶唑酮。该反应在室温下进行，并且可以接受各种官能团，例如 -X、-OMe、烯基和其他取代基。生成的恶唑酮通过脱羧还原提供获得 α-CF 3取代胺的途径。
• 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.
• Synthesis of Functionalized Oxazolones by a Sequence of Cu(II)- and Au(I)-Catalyzed Transformations
  作者：Florin M. Istrate、Andrea K. Buzas、Igor Dias Jurberg、Yann Odabachian、Fabien Gagosz

  DOI：10.1021/ol703077g

  日期：2008.3.1

  A study concerning a two-step sequence leading to the formation of diversely 1,5-disubstituted oxazolones is described. The mild conditions employed allow the efficient and rapid synthesis of a variety of such compounds via an initial Cu(II)-catalyzed coupling of a bromoalkyne with a secondary tert-butyloxycarbamate followed by a Au(I)-catalyzed cycloisomerization of the N-alkynyl tert-butyloxycarbamates thus obtained.