tert-Butyl (R)-5-hydroxy-3-oxooctanoate | 147849-61-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tert-Butyl (R)-5-hydroxy-3-oxooctanoate
• 英文别名: tert-butyl (5R)-5-hydroxy-3-oxooctanoate
• CAS: 147849-61-4
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: VEWWXSMOZHJHGU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-Butyl (R)-5-hydroxy-3-oxooctanoate 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 生成 (4R,6S)-6-Methoxycarbonylmethyl-2,2-dimethyl-4-propyl-1,3-dioxolane
  参考文献：
  名称：

  Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)86300-6
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， -78.0~30.0 ℃ 、10.13 MPa 条件下， 反应 1.75h， 生成 tert-Butyl (R)-5-hydroxy-3-oxooctanoate
  参考文献：
  名称：

  Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)86300-6

文献信息

• US8785690B2
  申请人：——

  公开号：US8785690B2

  公开（公告）日：2014-07-22
• 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.