(S)-N-(1-phenyl-2-butynyl)acetamide

• 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: (S)-N-(1-phenyl-2-butynyl)acetamide
• 英文别名: N-[(1R)-1-phenylbut-2-ynyl]acetamide
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: OJIZRKORNRCENZ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-[1-Phenyl-meth-(E)-ylidene]-acetamide 、 (10R)-B-propynyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 、 (1S,2S)-2-甲氨基-1-苯基丙-1-醇 以 二氯甲烷 、 乙腈 为溶剂， 反应 61.0h， 生成 9-((1S,2S)-pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane 、 (S)-N-(1-phenyl-2-butynyl)acetamide 、 (R)-N-(1-phenyl-2-butynyl)acetamide
  参考文献：
  名称：

  N-Propargylamides via the Asymmetric Michael Addition of B-Alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to N-Acylimines

  摘要：

  The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemistry. In several cases, 5 crystallizes in essentially pure form (97-99% ee) and a single-crystal X-ray structure was also obtained for 5g (R-1 = R-2 = Me, R-3 = o-Cl-C6C4). The process regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine.

  DOI：

  10.1021/ol0611595

文献信息

• <i>N</i>-Propargylamides via the Asymmetric Michael Addition of <i>B</i>-Alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to <i>N</i>-Acylimines
  作者：Ana Z. Gonzalez、Eda Canales、John A. Soderquist

  DOI：10.1021/ol0611595

  日期：2006.7.1

  The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemistry. In several cases, 5 crystallizes in essentially pure form (97-99% ee) and a single-crystal X-ray structure was also obtained for 5g (R-1 = R-2 = Me, R-3 = o-Cl-C6C4). The process regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine.