N-acetyl-N,3-diphenylprop-2-ynamide | 1039395-87-3

• 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: N-acetyl-N,3-diphenylprop-2-ynamide
• CAS: 1039395-87-3
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: PCSQDEOVKZAGSH-UHFFFAOYSA-N

物化性质

• 沸点：
  401.9±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-acetyl-N,3-diphenylprop-2-ynamide 在 Oxone 、 水 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 以69%的产率得到1-acetyl-3-bromo-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  ZnBr 2介导的丙酰胺酰胺的氧化螺-溴环化反应，用于合成3-溴-1-azaspiro [4.5] deca-3,6,9-三烯-2,8-二酮†

  摘要：

  本文已经描述了ZnBr 2介导的N-芳基丙酰胺酰胺的氧化螺-溴环化，用于高效合成3-溴-1-氮杂螺[4.5] deca-3,6,9-三烯-2,8-二酮。将一当量的水引入到最终产品中。该反应在室温下有效地进行，并且显示出优异的官能团耐受性。在标准条件下，3-溴-1-氧杂螺[4.5] deca-3,6,9-三烯-2,8-二酮和3-溴-1-氮杂螺[4.5] deca-3,6,9-trien-合成了8个。

  DOI：

  10.1039/c7ob00293a
• 作为产物：
  描述：

  异氰酸苯酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.5h， 生成 N-acetyl-N,3-diphenylprop-2-ynamide
  参考文献：
  名称：

  Catalytic oxidation/C–H functionalization of N-arylpropiolamides by means of gold carbenoids: concise route to 3-acyloxindoles

  摘要：

  一种高效的金卡宾促进的C-H官能化反应已被开发用于一步合成3-酰氧吲哚衍生物。该反应具有极佳的底物适用范围和显著的结构多样性拓展潜力。

  DOI：

  10.1039/c2cc31972a

文献信息

• Visible-light-mediated selective thiocyanation/ipso-cyclization/oxidation cascade for the synthesis of thiocyanato-containing azaspirotrienediones
  作者：Yuan Chen、Yu-Jue Chen、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2019.130763

  日期：2019.12

  visible-light-mediated metal-free thiocyanate radical addition/ipso-cyclization/oxidation cascade reaction for the synthesis of thiocyanato-containing azaspirotrienediones from N-phenylpropynamides is described. Cheap and readily available ammonium thiocyanate was used as a precursor to the thiocyanate free radical, which undergoes a radical addition reaction with the alkyne, followed by selective ipso-cyclization

  可见光介导的不含金属的硫氰酸盐基加/本位-cyclization /氧化级联含氰硫基azaspirotrienediones的从合成反应Ñ -phenylpropynamides进行说明。便宜和容易获得的硫氰酸铵用作前体硫氰酸自由基，其经历与炔自由基加成反应，然后进行选择性本位-cyclization和氧化，得到脱芳构化产品。没有检测到邻环化的产物。该反应在一锅中完成了C–S，CC和C = O键的合成，其中大量和可再生的空气氧气是唯一的牺牲试剂和氧气源。
• Palladium-Catalyzed Intramolecular 5-<i>exo</i>-<i>dig</i> Hydroarylations of <i>N</i>-Arylpropiolamides: Thermodynamics-Controlled Stereoselective Synthesis of 3-Methyleneoxindoles
  作者：Tao-Shan Jiang、Ri-Yuan Tang、Xing-Guo Zhang、Xin-Hua Li、Jin-Heng Li

  DOI：10.1021/jo901963g

  日期：2009.11.20

  has been developed for the stereoselective synthesis of 3-(monosubstituted methylene)oxindoles. In the presence of Pd(OAc)2 and dppf, a variety of N-arylpropiolamides successfully underwent the intramolecular hydroarylation reaction to afford the corresponding 3-(monosubstituted-methylene)oxindoles in moderate to excellent yields. It is noteworthy that the stereoselectivity of the reaction can be controlled

  已经开发了钯催化的N-芳基丙酰胺的分子内氢芳基化反应，用于3-（单取代的亚甲基）氧吲哚的立体选择性合成。在Pd（OAc）2和dppf的存在下，各种N-芳基丙酰胺成功地进行了分子内加氢芳基化反应，以中等至极好的收率得到了相应的3-（单取代-亚甲基）氧吲哚。值得注意的是，可以通过改变反应温度来控制反应的立体选择性。
• Palladium-Catalyzed C−H Functionalization of <i>N</i>-Arylpropiolamides with Aryliodonium Salts: Selective Synthesis of 3-(1-Arylmethylene)oxindoles
  作者：Shi Tang、Peng Peng、Ping Zhong、Jin-Heng Li

  DOI：10.1021/jo8008808

  日期：2008.7.1

  A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)(2) and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.
• Catalytic oxidation/C–H functionalization of N-arylpropiolamides by means of gold carbenoids: concise route to 3-acyloxindoles
  作者：Deyun Qian、Junliang Zhang

  DOI：10.1039/c2cc31972a

  日期：——

  An efficient catalytic C–H functionalization by means of gold carbenoids for the one-step synthesis of 3-acyloxindole derivatives has been developed. The reaction proceeds efficiently with extremely good substrate scope and significant opportunities for structural diversification.

  一种高效的金卡宾促进的C-H官能化反应已被开发用于一步合成3-酰氧吲哚衍生物。该反应具有极佳的底物适用范围和显著的结构多样性拓展潜力。
• ZnBr₂-Mediated oxidative spiro-bromocyclization of propiolamide for the synthesis of 3-bromo-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  作者：Yicheng He、Guanyinsheng Qiu

  DOI：10.1039/c7ob00293a

  日期：——

  ZnBr2-Mediated oxidative spiro-bromocyclization of N-arylpropiolamide has been described herein for the synthesis of 3-bromo-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione with high efficiency. One equivalent of water was introduced into the final product. The reaction efficiently proceeded at room temperature, and an excellent tolerance of functional groups was demonstrated. Under standard conditions

  本文已经描述了ZnBr 2介导的N-芳基丙酰胺酰胺的氧化螺-溴环化，用于高效合成3-溴-1-氮杂螺[4.5] deca-3,6,9-三烯-2,8-二酮。将一当量的水引入到最终产品中。该反应在室温下有效地进行，并且显示出优异的官能团耐受性。在标准条件下，3-溴-1-氧杂螺[4.5] deca-3,6,9-三烯-2,8-二酮和3-溴-1-氮杂螺[4.5] deca-3,6,9-trien-合成了8个。