(2R,E)-2,5-dihydoroxy-2-methyl-3-dodecenamide | 1286783-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,E)-2,5-dihydoroxy-2-methyl-3-dodecenamide
• CAS: 1286783-78-5
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: HXSWKPKJCXBEBU-YVFJSFFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  83.55
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,E)-2,5-dihydoroxy-2-methyl-3-dodecenamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.7h， 以96%的产率得到(R,E)-2-hydroxy-2-methyl-5-oxo-3-dodecenamide
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n
• 作为产物：
  描述：

  (R,E)-2-carbamoyl-5-oxo-3-dodecen-2-yl benzoate 在 sodium tetrahydroborate 、 lithium methanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.5h， 生成 (2R,E)-2,5-dihydoroxy-2-methyl-3-dodecenamide
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n