(3R,6R,7R,7aS)-6,7-Dihydroxy-6-methyl-3-phenyl-7a-propyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one | 284026-44-4

• 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: (3R,6R,7R,7aS)-6,7-Dihydroxy-6-methyl-3-phenyl-7a-propyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
• 英文别名: (3R,6R,7R,7aS)-6,7-dihydroxy-6-methyl-3-phenyl-7a-propyl-3,7-dihydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 284026-44-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: XKKOAJUVHFKAHR-CLWVCHIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,6R,7R,7aS)-6,7-Dihydroxy-6-methyl-3-phenyl-7a-propyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 在 lead(IV) acetate 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 potassium carbonate 作用下， 以 叔丁醇 、 苯 为溶剂， 生成 (2R,4S)-3-(2-Oxo-propionyl)-2-phenyl-4-propyl-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  A New Approach for Construction of Quarternary Chiral Centers: Preparation of a-Branched Serine Derivatives

  摘要：

  In the presence of a Lewis acid, the Michael-type reaction of (3R)-5-tert-butyldimethylsiloxy-3-phenyl-1H-pyrrolo[1,2-c]oxazole (1) with nitro olefins smoothly occurred to give 7a-alkylated pyrrolo[1,2-c]oxazol-5-ones (2) in good yields. The products (2) were successfully transformed to a alpha-branched serine derivatives via reductive denitration followed by lactam-ring cleavage.

  DOI：

  10.3987/com-00-8863
• 作为产物：
  描述：

  (3R,7aR)-6-Methyl-3-phenyl-7a-propyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 叔丁醇 为溶剂， 以60%的产率得到(3R,6R,7R,7aS)-6,7-Dihydroxy-6-methyl-3-phenyl-7a-propyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
  参考文献：
  名称：

  A New Approach for Construction of Quarternary Chiral Centers: Preparation of a-Branched Serine Derivatives

  摘要：

  In the presence of a Lewis acid, the Michael-type reaction of (3R)-5-tert-butyldimethylsiloxy-3-phenyl-1H-pyrrolo[1,2-c]oxazole (1) with nitro olefins smoothly occurred to give 7a-alkylated pyrrolo[1,2-c]oxazol-5-ones (2) in good yields. The products (2) were successfully transformed to a alpha-branched serine derivatives via reductive denitration followed by lactam-ring cleavage.

  DOI：

  10.3987/com-00-8863

文献信息

• A New Approach for Construction of Quarternary Chiral Centers: Preparation of a-Branched Serine Derivatives
  作者：Hidemitsu Uno、Hidemitsu Uno、Ken-ichi Kasahara、Noboru Ono

  DOI：10.3987/com-00-8863

  日期：——

  In the presence of a Lewis acid, the Michael-type reaction of (3R)-5-tert-butyldimethylsiloxy-3-phenyl-1H-pyrrolo[1,2-c]oxazole (1) with nitro olefins smoothly occurred to give 7a-alkylated pyrrolo[1,2-c]oxazol-5-ones (2) in good yields. The products (2) were successfully transformed to a alpha-branched serine derivatives via reductive denitration followed by lactam-ring cleavage.