(4RS,5RS,6SR)-2-benzylidenamino-4-(2-benzylidenamino-1-methyl-1H-imidazol-5-yl)-5,6-bis(hydroxymethyl)-1-methyl-4,5,6,7-tetrahydro-1H-benzimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4RS,5RS,6SR)-2-benzylidenamino-4-(2-benzylidenamino-1-methyl-1H-imidazol-5-yl)-5,6-bis(hydroxymethyl)-1-methyl-4,5,6,7-tetrahydro-1H-benzimidazole
• 英文别名: [(5S,6S,7R)-2-(benzylideneamino)-7-[2-(benzylideneamino)-3-methylimidazol-4-yl]-6-(hydroxymethyl)-3-methyl-4,5,6,7-tetrahydrobenzimidazol-5-yl]methanol
• 化学式: C₂₈H₃₀N₆O₂
• 分子量: 482.585
• InChiKey: CNIARIOCPUHZPU-TZBSWOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4RS,5RS,6SR)-2-benzylidenamino-4-(2-benzylidenamino-1-methyl-1H-imidazol-5-yl)-5,6-bis(hydroxymethyl)-1-methyl-4,5,6,7-tetrahydro-1H-benzimidazole 在 叠氮磷酸二苯酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 以95%的产率得到(4RS,5RS,6SR)-5,6-bis(azidomethyl)-2-benzylidenamino-4-(2-benzylidenamino-1-methyl-1H-imidazol-5-yl)-1-methyl-4,5,6,7-tetrahydro-1H-benzimidazole
  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：

  3-methyl-2-phenylsulfanylimidazole-4-carbaldehyde 在 palladium on activated charcoal 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 仲丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cesium fluoride 、 lithium chloride 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 环己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 xylene 为溶剂， -40.0~140.0 ℃ 、101.33 kPa 条件下， 反应 79.02h， 生成 (4RS,5RS,6SR)-2-benzylidenamino-4-(2-benzylidenamino-1-methyl-1H-imidazol-5-yl)-5,6-bis(hydroxymethyl)-1-methyl-4,5,6,7-tetrahydro-1H-benzimidazole
  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

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.