(R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide | 139209-88-4

• 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: (R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide
• CAS: 139209-88-4
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: NOFRXYFDLNVAOR-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,5-二酮己酸甲酯 在 palladium on activated charcoal 、 Ru₂Cl₄((R)-binap)(Et₃N) 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 反应 51.0h， 生成 (R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Asymmetric hydrogenation of methyl 3,5-dioxohexanoate catalyzed by ru-binap complex: a short step asymmetric synthesis of dihydro-60methyl-2-H-pyran-2-one

  摘要：

  Hydrogenation of methyl 3,5-dioxohexanoate 3 using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyester 9, which was then converted into unsaturated lactone 4. The pathway of the hydrogenation reaction was also investigated.

  DOI：

  10.1016/0040-4039(91)80569-r

文献信息

• Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones
  作者：Liming Shao、Hiroyuki Kawano、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1016/s0040-4020(01)86300-6

  日期：1993.3

  Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.