ditert-butyl 2-[(2S,3R)-2-hydroxy-1-morpholin-4-yl-1-oxopentan-3-yl]propanedioate | 1072808-26-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ditert-butyl 2-[(2S,3R)-2-hydroxy-1-morpholin-4-yl-1-oxopentan-3-yl]propanedioate
• CAS: 1072808-26-4
• 化学式: C₂₀H₃₅NO₇
• 分子量: 401.5
• InChiKey: IPVISAXWUPAPRM-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ditert-butyl 2-[(2S,3R)-2-hydroxy-1-morpholin-4-yl-1-oxopentan-3-yl]propanedioate 在 甲酸 作用下， 反应 5.0h， 以100%的产率得到(3S,4R,5S)-4-ethyl-5-(morpholine-4-carbonyl)-2-oxooxolane-3-carboxylic acid
  参考文献：
  名称：

  Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates

  摘要：

  An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

  DOI：

  10.1021/ja805680z
• 作为产物：
  描述：

  di-tert-butyl 2-(1-morpholino-1,2-dioxopentan-3-yl)malonate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到ditert-butyl 2-[(2S,3R)-2-hydroxy-1-morpholin-4-yl-1-oxopentan-3-yl]propanedioate
  参考文献：
  名称：

  Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates

  摘要：

  An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

  DOI：

  10.1021/ja805680z