N-(3-methoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide | 475273-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3-methoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide
• 英文别名: (Z)-N-[(3-methoxyphenyl)methyl]-N-methyl-3-phenylsulfanylprop-2-enamide
• CAS: 475273-32-6
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: ZGWIFYOZYFZSDL-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-methoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以77%的产率得到8-methoxy-2-methyl-1,2-dihydrobenz[c]azepin-3-one
  参考文献：
  名称：

  Synthesis of 1,2-Dihydrobenz[c]azepin-3-one via Acid-catalyzed Cyclization of N-Arylmethyl-N-methyl-3-phenylsulfanylacrylamide

  摘要：

  Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structures of the substrates. The route provides a simple method of preparing 6-methoxy-(7e), 8-methoxy-(7d), 6,8-dimethoxy-(7f), and 8,9-dimethoxy-N-methyl-1,2-dihydrobenz[c]azepin-3-ones (7g), although the scope is limited by some side reactions.

  DOI：

  10.3987/com-02-9472
• 作为产物：
  描述：

  p-nitrophenyl cis-3-phenylsulfanylacrylate 在 氢氧化钾 、 四乙基溴化铵 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 64.0h， 生成 N-(3-methoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide
  参考文献：
  名称：

  Synthesis of 1,2-Dihydrobenz[c]azepin-3-one via Acid-catalyzed Cyclization of N-Arylmethyl-N-methyl-3-phenylsulfanylacrylamide

  摘要：

  Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structures of the substrates. The route provides a simple method of preparing 6-methoxy-(7e), 8-methoxy-(7d), 6,8-dimethoxy-(7f), and 8,9-dimethoxy-N-methyl-1,2-dihydrobenz[c]azepin-3-ones (7g), although the scope is limited by some side reactions.

  DOI：

  10.3987/com-02-9472

文献信息

• Synthesis of 1,2-Dihydrobenz[c]azepin-3-one via Acid-catalyzed Cyclization of N-Arylmethyl-N-methyl-3-phenylsulfanylacrylamide
  作者：Yoshie Horiguchi、Toshiaki Saitoh、Tomoko Kashiwagi、Lisa Katura、Mayumi Itagaki、Jun Toda、Takehiro Sano

  DOI：10.3987/com-02-9472

  日期：——

  Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structures of the substrates. The route provides a simple method of preparing 6-methoxy-(7e), 8-methoxy-(7d), 6,8-dimethoxy-(7f), and 8,9-dimethoxy-N-methyl-1,2-dihydrobenz[c]azepin-3-ones (7g), although the scope is limited by some side reactions.