(E)-N-(2-bromophenyl)-N-tert-butoxycarbonyl-(4-phenylbut-3-en-1-yn-1-yl)amine | 1440672-30-9

• 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: (E)-N-(2-bromophenyl)-N-tert-butoxycarbonyl-(4-phenylbut-3-en-1-yn-1-yl)amine
• 英文别名: (E)-tert-butyl (2-bromophenyl)(4-phenylbut-3-en-1-yn-1-yl)carbamate；tert-butyl N-(2-bromophenyl)-N-[(E)-4-phenylbut-3-en-1-ynyl]carbamate
• CAS: 1440672-30-9
• 化学式: C₂₁H₂₀BrNO₂
• 分子量: 398.299
• InChiKey: HJVGAFIQOYQVDU-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E)-N-(2-bromophenyl)-N-tert-butoxycarbonyl-(4-phenylbut-3-en-1-yn-1-yl)amine 在 叔丁基锂 、 copper(I) cyanide di(lithium chloride) 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 反应 14.0h， 以54%的产率得到N‐tert‐butoxycarbonyl‐3‐styrylindole
  参考文献：
  名称：

  Intramolecular Carbocupration of N-Aryl-ynamides: A Modular Indole Synthesis

  摘要：

  A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides Is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.

  DOI：

  10.1021/ol4013298
• 作为产物：
  描述：

  (4-bromobut-1-en-3-ynyl)benzene 、 N-(叔丁氧基羰基)-2-溴苯胺 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以53%的产率得到(E)-N-(2-bromophenyl)-N-tert-butoxycarbonyl-(4-phenylbut-3-en-1-yn-1-yl)amine
  参考文献：
  名称：

  Intramolecular Carbocupration of N-Aryl-ynamides: A Modular Indole Synthesis

  摘要：

  A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides Is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.

  DOI：

  10.1021/ol4013298

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。
• Palladium-Catalyzed Intramolecular Cyclization of Ynamides: Synthesis of 4-Halo-oxazolones
  作者：Hai Huang、Guangke He、Guohao Zhu、Xiaolin Zhu、Shineng Qiu、Hongjun Zhu

  DOI：10.1021/acs.joc.5b00071

  日期：2015.4.3

  A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the

  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。