tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate | 147849-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate
• CAS: 147849-58-9
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: DYMMPVLMFHDPPA-CYBMUJFWSA-N

物化性质

• 沸点：
  379.8±32.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate 在 sodium tetrahydroborate 、 三乙基硼 、 硫酸 、 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 11.75h， 生成 (R)-6-Benzyloxymethyl-5,6-dihydro-2-pyrone
  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：

  醋酸叔丁酯 在 Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃ 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， -78.0~30.0 ℃ 、10.13 MPa 条件下， 生成 tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate
  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