N-(3,4-dimethoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide | 475273-35-9

• 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-(3,4-dimethoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide
• 英文别名: (Z)-N-[(3,4-dimethoxyphenyl)methyl]-N-methyl-3-phenylsulfanylprop-2-enamide
• CAS: 475273-35-9
• 化学式: C₁₉H₂₁NO₃S
• 分子量: 343.447
• InChiKey: PCEXTUJGZAOZAS-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以1%的产率得到1,2-dihydro-7,8-dimethoxy-2-methyl-3H-2-benzazepin-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：

  (2Z)-3-(phenylthio)acrylic acid 在 氢氧化钾 、 四乙基溴化铵 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 65.0h， 生成 N-(3,4-dimethoxyphenyl)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.