benzyl N-[(1R)-3-oxo-1-phenyl-2-propanoylpentyl]carbamate | 1149349-32-5

• 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: benzyl N-[(1R)-3-oxo-1-phenyl-2-propanoylpentyl]carbamate
• CAS: 1149349-32-5
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: JWWDGNIIRNFDRS-NRFANRHFSA-N

物化性质

• 沸点：
  542.5±50.0 °C(predicted)
• 密度：
  1.138±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-庚烷二酮 、 benzyl N-benzylidenecarbamate 在 1,1'-联萘-2,2'-二磺酸 、 2,6-二苯基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到benzyl N-[(1R)-3-oxo-1-phenyl-2-propanoylpentyl]carbamate
  参考文献：
  名称：

  用于不对称直接曼尼希型反应的高度实用的BINOL衍生酸基复合盐催化剂

  摘要：

  亚胺和1，3-二羰基化合物之间的催化不对称直接曼尼希型反应是有机化学中最重要的碳-碳键形成反应之一。所得的曼尼希加合物可以有效地转化为药学上有用的旋光性β-氨基酮，β-氨基酯，β-内酰胺等。在我们研究用于不对称反应的手性酸-碱结合盐催化剂的过程中，我们开发了一系列简单，实用的手性BINOL衍生的盐催化剂，例如手性吡啶鎓1,1'-联萘-2,2'-二磺酸盐1，手性联萘甲酸锂（I）2，手性联萘甲酸镁（II）（3） ，手性磷酸钙（II）4和手性磷酸5，对直接曼尼希型反应特别有效。 1引言 2 1,1'-联萘-2,2'-二磺酸（BINSA）-吡啶鎓盐 3萘甲酸锂（I）盐 4萘甲酸镁（II）盐 5磷酸钙（II）盐和手性磷酸 6。结论 酸碱复合盐催化剂-亚胺-不对称催化-1,3-二羰基化合物-直接曼尼希型反应

  DOI：

  10.1055/s-0030-1258296

文献信息

• PROCESS FOR MANUFACTURING DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALST, PROCESS FOR MANUFACTURING BETA-AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE
  申请人：Ishihara Kazuaki

  公开号：US20100249431A1

  公开（公告）日：2010-09-30

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1′-binaphthyl-2,2′-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80° C. for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1′-binaphthyl-2,2′-disulfonate. The (R)-1,1′-binaphthyl-2,2′-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH 2 Cl 2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0° C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0° C. for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.