(E)-N-benzhydryl-3-(1-benzyl-1H-imidazol-4-yl)-N-hydroxy-2-propenamide | 954426-14-3

• 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: (E)-N-benzhydryl-3-(1-benzyl-1H-imidazol-4-yl)-N-hydroxy-2-propenamide
• 英文别名: (E)-N-benzhydryl-3-(1-benzylimidazol-4-yl)-N-hydroxyprop-2-enamide
• CAS: 954426-14-3
• 化学式: C₂₆H₂₃N₃O₂
• 分子量: 409.488
• InChiKey: WCUVNPXDEZTKEA-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-benzhydryl-3-(1-benzyl-1H-imidazol-4-yl)-N-hydroxy-2-propenamide 在 tris(dibenzylideneacetone)dipalladium (0) 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 (+/-)-(4aS,8aR,9S)-6-benzhydryl-1-benzyl-9-(1-benzyl-1H-imidazol-4-yl)-5-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[5,4-f]benzimidazole
  参考文献：
  名称：

  Studies toward the Total Synthesis of Axinellamine and Massadine

  摘要：

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.

  DOI：

  10.1021/ol0711568
• 作为产物：
  描述：

  二苯甲酮肟 在 盐酸 、 sodium cyanoborohydride 、 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E)-N-benzhydryl-3-(1-benzyl-1H-imidazol-4-yl)-N-hydroxy-2-propenamide
  参考文献：
  名称：

  Studies toward the Total Synthesis of Axinellamine and Massadine

  摘要：

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.

  DOI：

  10.1021/ol0711568

文献信息

• Studies toward the Total Synthesis of Axinellamine and Massadine
  作者：Rasapalli Sivappa、Nora M. Hernandez、Yong He、Carl J. Lovely

  DOI：10.1021/ol0711568

  日期：2007.9.1

  Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.