(3aS,5R,6S,7aR)-5,6-Diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one | 827045-22-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3aS,5R,6S,7aR)-5,6-Diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one
• 英文别名: (3aR,5S,6R,7aS)-5,6-diphenyl-1,3,3a,5,6,7a-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one
• CAS: 827045-22-7
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: QLZGKNDQIQWLIZ-SYMSYNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,5R,6S,7aR)-5,6-Diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 (-)-aminoalcohol compound 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3aS,5R,6S,7aR)-1-Acetyl-5,6-diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one
  参考文献：
  名称：

  Catalytic dissymmetrization of meso-2-imidazolidinones: alternative route to chiral synthons for 1,2-diamines

  摘要：

  The chiral functionalization of a simple heterocycle, 1,3-dihydro-2-imidazolone, was achieved by the highly enantioselective monodeacylation of meso-1,3-diacetyl-2-imidazolidinones via an oxazaborolidine-catalyzed borane reduction. This kinetically controlled dissymmetrization is sufficiently effective to provide a synthetic route to either enantiomer of (4S, 5s)- or (4R, 5R)-4,5-dimethoxy-2-imidazolidinone derivatives, which serve as chiral synthons for threo-1,2-diamines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.129
• 作为产物：
  描述：

  (1S,2R)-1,2-diphenylethane-1,2-diol 、 4,5-二甲氧基咪唑烷-2-酮 在 BF*OEt₂ 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(3aS,5R,6S,7aR)-5,6-Diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one
  参考文献：
  名称：

  Catalytic dissymmetrization of meso-2-imidazolidinones: alternative route to chiral synthons for 1,2-diamines

  摘要：

  The chiral functionalization of a simple heterocycle, 1,3-dihydro-2-imidazolone, was achieved by the highly enantioselective monodeacylation of meso-1,3-diacetyl-2-imidazolidinones via an oxazaborolidine-catalyzed borane reduction. This kinetically controlled dissymmetrization is sufficiently effective to provide a synthetic route to either enantiomer of (4S, 5s)- or (4R, 5R)-4,5-dimethoxy-2-imidazolidinone derivatives, which serve as chiral synthons for threo-1,2-diamines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.129