5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole | 460990-46-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole
• 英文别名: ethyl (E)-3-[3-(methoxymethyl)-2-phenylsulfanylimidazol-4-yl]prop-2-enoate
• CAS: 460990-46-9
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: VHQOWVGGZSFTGC-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以71%的产率得到4-[(E)-2-(ethoxycarbonyl)ethenyl]-2-phenylsulfanyl-1H-imidazole
  参考文献：
  名称：

  Homonuclear Diels–Alder dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to synthesis of 12,12′-dimethylageliferin

  摘要：

  Homonuclear Diels-Alder dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, which is the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.027
• 作为产物：
  描述：

  1-(methoxymethyl)-2-(phenylthio)-1H-imidazole 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙腈 为溶剂， 生成 5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methoxymethyl-2-phenylsulfanyl-1H-imidazole
  参考文献：
  名称：

  Novel Diels–Alder-type dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to biomimetic synthesis of 12,12′-dimethylageliferin

  摘要：

  Diels-Alder-type dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00782-7

文献信息

• Novel Diels–Alder-type dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to biomimetic synthesis of 12,12′-dimethylageliferin
  作者：Ikuo Kawasaki、Norihiro Sakaguchi、Norie Fukushima、Naoko Fujioka、Fumi Nikaido、Masayuki Yamashita、Shunsaku Ohta

  DOI：10.1016/s0040-4039(02)00782-7

  日期：2002.6

  Diels-Alder-type dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Homonuclear Diels–Alder dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to synthesis of 12,12′-dimethylageliferin
  作者：Ikuo Kawasaki、Norihiro Sakaguchi、Abdul Khadeer、Masayuki Yamashita、Shunsaku Ohta

  DOI：10.1016/j.tet.2006.08.027

  日期：2006.10

  Homonuclear Diels-Alder dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, which is the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (c) 2006 Elsevier Ltd. All rights reserved.