(3aS,5R,6S,7aR)-1,3-Diacetyl-5,6-diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one | 827045-27-2

• 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: (3aS,5R,6S,7aR)-1,3-Diacetyl-5,6-diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one
• 英文别名: (3aS,5R,6S,7aR)-1,3-diacetyl-5,6-diphenyl-3a,5,6,7a-tetrahydro-[1,4]dioxino[2,3-d]imidazol-2-one
• CAS: 827045-27-2
• 化学式: C₂₁H₂₀N₂O₅
• 分子量: 380.4
• InChiKey: HAOFTFWHEWZCER-JVSBHGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,5R,6S,7aR)-1,3-Diacetyl-5,6-diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one 在 dimethyl sulfide borane 、 (-)-aminoalcohol compound 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3aR,5R,6S,7aS)-1-Acetyl-5,6-diphenyl-hexahydro-[1,4]dioxino[2,3-d]imidazol-2-one 、 (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 在 4-二甲氨基吡啶 、 BF*OEt₂ 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3aS,5R,6S,7aR)-1,3-Diacetyl-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