N-benzhydryl-N-[3-(1-benzyl-1H-imidazol-4-yl)allyloxy]-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)acrylamide | 954426-21-2

• 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-benzhydryl-N-[3-(1-benzyl-1H-imidazol-4-yl)allyloxy]-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)acrylamide
• 英文别名: (E)-N-benzhydryl-N-[(E)-3-(1-benzylimidazol-4-yl)prop-2-enoxy]-3-[1-(dimethylsulfamoyl)imidazol-4-yl]prop-2-enamide
• CAS: 954426-21-2
• 化学式: C₃₄H₃₄N₆O₄S
• 分子量: 622.748
• InChiKey: OHWXGPCREZTOPY-XXKASZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-benzhydryl-N-[3-(1-benzyl-1H-imidazol-4-yl)allyloxy]-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)acrylamide 在 samarium diiodide 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 60.0h， 生成 (+/-)-(5S,6R,7S)-N-benzhydryl-1-dimethylsulfamoyl-7-(1-benzyl-1H-imidazol-4-yl)-4,5,6,7-tetrahydro-1H-benzimidazole-6-carboxamide
  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 tris(dibenzylideneacetone)dipalladium (0) 盐酸 、 sodium cyanoborohydride 、 sodium sulfate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 N-benzhydryl-N-[3-(1-benzyl-1H-imidazol-4-yl)allyloxy]-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)acrylamide
  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.