N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-acetamide | 574743-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-acetamide
• CAS: 574743-55-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: VKAGTABOPHRYTI-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-acetamide 、 13-Oct-1-ynyl-10,16-diphenyl-12,14-dioxa-13-borapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (R)-N-(1-(4-methoxyphenyl)non-2-ynyl)acetamide 、 (S)-N-(1-(4-methoxyphenyl)non-2-ynyl)acetamide
  参考文献：
  名称：

  Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates

  摘要：

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.

  DOI：

  10.1021/ol0523087
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 正己烷 、 氯仿 为溶剂， 反应 4.0h， 生成 N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-acetamide
  参考文献：
  名称：

  Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates

  摘要：

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.

  DOI：

  10.1021/ol0523087

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.