N-benzyl-4-phenyl-3-butynamide | 518061-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyl-4-phenyl-3-butynamide
• 英文别名: N-benzyl-4-phenylbut-3-ynamide
• CAS: 518061-69-3
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: NWKGONAUNHGVOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-N-苄基-乙酰胺 、 苯基乙炔三丁基锡 在 二(氰基苯)二氯化钯 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 N-benzyl-4-phenyl-3-butynamide
  参考文献：
  名称：

  Alkynylation of α-halocarbonyl compounds—a Stille-type cross-coupling for the formation of C(sp)–C(sp³) bonds under neutral conditions

  摘要：

  本文描述了一种对易得的α-卤酯和酰胺进行直接炔基化的方法，取得了高产率；在中性条件下实现了从二炔生成的转变到炔基化产物。

  DOI：

  10.1039/b703221h

文献信息

• Triethylborane-Induced Radical Reaction of Alkynylgallium with<i>α</i>-Halo Carbonyl Compounds
  作者：Shin-ichi Usugi、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1246/bcsj.75.2687

  日期：2002.12

  Treatment of terminal acetylenes with butyllithium, followed by an addition of gallium trichloride, afforded the corresponding alkynylgallium reagents. The reaction of the resulting alkynylgallium with α-halo carbonyl compounds in the presence of triethylborane as a radical initiator provided β,γ-acetylenic carbonyl compounds in good yields.

  用丁基锂处理末端乙炔，然后加入三氯化镓，得到相应的炔基镓试剂。在作为自由基引发剂的三乙基硼烷存在下，所得炔基镓与α-卤代羰基化合物的反应以良好的产率提供了β,γ-炔羰基化合物。
• Pd-Catalyzed Alkynylation of 2-Chloroacetates and 2-Chloroacetamides with Potassium Alkynyltrifluoroborates
  作者：Gary A. Molander、Kaitlin M. Traister

  DOI：10.1021/ol402391z

  日期：2013.10.4

  The synthesis of beta,gamma-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargyl esters and amides were obtained In high yields using a low catalyst loading, and the substrate scope of the reaction has been significantly improved over previous methods.
• Alkynylation of α-halocarbonyl compounds—a Stille-type cross-coupling for the formation of C(sp)–C(sp³) bonds under neutral conditions
  作者：Wei Shi、Chao Liu、Zai Yu、Aiwen Lei

  DOI：10.1039/b703221h

  日期：——

  A direct alkynylation of readily available α-halo esters and amides with high yields is described herein; a distinct switch from diyne formation to alkynylation products was attained under neutral conditions.

  本文描述了一种对易得的α-卤酯和酰胺进行直接炔基化的方法，取得了高产率；在中性条件下实现了从二炔生成的转变到炔基化产物。