(+/-)-(4aS,8aR,9S)-7-benzhydryl-1-dimethylsulfamoyl-9-{1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl}-8-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[4,5-f]benzimidazole

• 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: (+/-)-(4aS,8aR,9S)-7-benzhydryl-1-dimethylsulfamoyl-9-{1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl}-8-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[4,5-f]benzimidazole
• 英文别名: 4-[(4aS,8aS,9R)-7-benzhydryl-8-oxo-1-(2-trimethylsilylethoxymethyl)-4a,5,8a,9-tetrahydro-4H-imidazo[4,5-g][2,3]benzoxazin-9-yl]-N,N-dimethylimidazole-1-sulfonamide
• 化学式: C₃₃H₄₂N₆O₅SSi
• 分子量: 662.885
• InChiKey: PBYHGUQFMABAMH-XUEBXJBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-)-(4aS,8aR,9S)-7-benzhydryl-1-dimethylsulfamoyl-9-{1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl}-8-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[4,5-f]benzimidazole 在 3-(4-nitrophenyl)-2-phenylsulfonyloxaziridine 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以61%的产率得到
  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 、 甲苯 为溶剂， 反应 52.0h， 生成 (+/-)-(4aS,8aR,9S)-7-benzhydryl-1-dimethylsulfamoyl-9-{1-[2-(trimethylsilyl)ethoxymethyl]-1H-imidazol-4-yl}-8-oxo-4,4a,7a,8-tetrahydro-1H-[1,2]oxazino[4,5-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

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.