(-)-ethyl (2E)-4-<((2'R)-2'-(hydroxymethyl)butanoyl)oxy>-2-butenoate | 163457-36-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (-)-ethyl (2E)-4-<((2'R)-2'-(hydroxymethyl)butanoyl)oxy>-2-butenoate
• 英文别名: [(E)-4-ethoxy-4-oxobut-2-enyl] (2R)-2-(hydroxymethyl)butanoate
• CAS: 163457-36-1
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: XISAEGFZJJRHJA-VUHVRTRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-ethyl (2E)-4-<((2'R)-2'-(hydroxymethyl)butanoyl)oxy>-2-butenoate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以95%的产率得到(-)-ethyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone 在 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 双氧水 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (-)-ethyl (2E)-4-<((2'R)-2'-(hydroxymethyl)butanoyl)oxy>-2-butenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e