(1R,3S,7R,9S)-4,6-diacetyl-2,8-dioxa-4,6-diazatricyclo[7.4.0.03,7]tridecan-5-one | 827045-25-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (1R,3S,7R,9S)-4,6-diacetyl-2,8-dioxa-4,6-diazatricyclo[7.4.0.03,7]tridecan-5-one
• CAS: 827045-25-0
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: ZAZMNLPORJGIOV-IWDIQUIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (1R,3S,7R,9S)-4,6-diacetyl-2,8-dioxa-4,6-diazatricyclo[7.4.0.03,7]tridecan-5-one 在 dimethyl sulfide borane 、 (-)-aminoalcohol compound 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以55%的产率得到(1S,3R,7S,9R)-4-acetyl-2,8-dioxa-4,6-diazatricyclo[7.4.0.03,7]tridecan-5-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：

  cis-1,2-cyclohexane 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 (1R,3S,7R,9S)-4,6-diacetyl-2,8-dioxa-4,6-diazatricyclo[7.4.0.03,7]tridecan-5-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