5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methyl-2-phenylsulfanyl-1H-imidazole | 460990-31-2

• 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-methyl-2-phenylsulfanyl-1H-imidazole
• 英文别名: ethyl 3-(1-methyl-2-phenylsulfanyl-1H-imidazol-5-yl)propenoate；ethyl (E)-3-(3-methyl-2-phenylsulfanylimidazol-4-yl)prop-2-enoate
• CAS: 460990-31-2
• 化学式: C₁₅H₁₆N₂O₂S
• 分子量: 288.37
• InChiKey: RBCDQJFKRAWLDP-MDZDMXLPSA-N

物化性质

• 沸点：
  477.1±37.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(ethoxycarbonyl)ethenyl]-1-methyl-2-phenylsulfanyl-1H-imidazole 在 palladium on activated charcoal 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 仲丁基锂 、 三苯基膦 、 cesium fluoride 、 nickel(I) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 xylene 为溶剂， 反应 36.0h， 生成
  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
• 作为产物：
  描述：

  1-methyl-2-phenylsulfanyl-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-methyl-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

• Regio- and Stereoselective Head-to-Head Photo[2+2]cycloaddition of 3-(1-Methyl-2-phenylsulfanyl-1H-imidazol-5-yl)propenoates
  作者：Shunsaku Ohta、Abdul Khadeer、Akiko Kakuno、Ikuo Kawasaki、Masayuki Yamashita

  DOI：10.3987/com-06-10964

  日期：——

  Head-to-head photo[2+2]cycloaddition of 1, omega -di[3-(1-methyl-2-phenylsulfanyl-1H-imidazol-5-yl)propenoyloxy]alkylenes smoothly proceeded under irradiation of a high-pressure mercury lamp to give cyclobutane compounds regio- and stereoselectively. The stereochemistry of these cyclobutanes was determined as beta-form.
• 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.