N-benzyl-2,3-dihydro-2-phenyl-4-pyridone | 141120-45-8

• 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: N-benzyl-2,3-dihydro-2-phenyl-4-pyridone
• 英文别名: (R)-N-benzyl-2,3-dihydro-2-phenyl-4-pyridone；(R)-1-benzyl-2,3-dihydro-2-phenylpyridin-4(1H)-one；(2R)-1-benzyl-2-phenyl-2,3-dihydropyridin-4-one
• CAS: 141120-45-8
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: BHFYWYJDBPMYKC-GOSISDBHSA-N

物化性质

• 沸点：
  434.3±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,3-dihydro-2-phenyl-4-pyridone 生成 (R)-2-phenylpiperidine
  参考文献：
  名称：

  Asymmetric aza-Diels-Alder reaction mediated by chiral boron reagent

  摘要：

  An asymmetric aza-Diels-Alder reaction of an imines mediated by an in situ generated chiral boron complex is described. The method is successful with several aldimines and affords products of up to 90% ee.

  DOI：

  10.1021/jo00038a003
• 作为产物：
  描述：

  苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 magnesium sulfate 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 N-benzyl-2,3-dihydro-2-phenyl-4-pyridone
  参考文献：
  名称：

  不对称的aza-Diels-Alder反应：手性路易斯酸介导的亚胺对映体和非对映体选择性反应

  摘要：

  开发了一种有效的使用手性硼介体的不对称aza-Diels-Alder反应。其成功的关键是使用由（R）-或（S）-联萘酚和B（OPh）3原位制备的手性硼配合物。前手性亚胺的对映体反应可提供高达90％ee的产物。使用α-苄基胺作为手性助剂，可以实现对脂肪族和芳香族亚胺几乎完全非对映选择性的手性亚胺的双不对称诱导。该方法适用于高效合成哌啶生物碱的鸟嘌呤和芥氨酸。

  DOI：

  10.1016/s0040-4020(01)80532-9

文献信息

• Regulation of Orthogonal Functions in a Dual Catalyst System. Subservient Role of a Nonchiral Lewis Acid in an Asymmetric Catalytic Heteroatom Diels−Alder Reaction
  作者：Cory A. Newman、Jon C. Antilla、Pei Chen、Alexander V. Predeus、Lee Fielding、William D. Wulff

  DOI：10.1021/ja069019d

  日期：2007.6.13

  A catalytic asymmetric heteroatom Diels-Alder reaction of unactivated imines with Danishefsky's diene is described which gives high asymmetric induction for N-benzhydryl imines derived from a variety of aldehydes. The catalyst is derived from B(OPh)(3) and the VAPOL ligand and gives good induction, but the reaction stalls and does not give high conversion (similar to 50%). It was found that in the presence of both the chiral catalyst and excess amounts of B(OPh)(3) the reaction proceeds to completion and gives high yields of the dihydropiperidinone product. Despite the presence of large quantities of the nonchiral Lewis acid B(OPh)(3), the asymmetric induction of the product remains constant (90% ee) as the amount of B(OPh)(3) is steadily increased and does not drop off until the ratio of B(OPh)(3) to VAPOL is 100:1 (82% ee). These observations are interpreted as involving highly separated and different activities for the chiral and nonchiral Lewis acids present in the reaction. Specifically, the excess B(OPh)(3) serves to bind to the product and release the chiral catalyst to turnover more starting material. The B(OPh)(3) does not compete in turning over the starting material, and a series of binding studies reveal that this is likely due to a combination of two factors. The binding studies reveal that the chiral catalyst binds to the starting imine 7 times more strongly than does B(OPh)(3). However, in order to explain the constant asymmetric induction observed despite the addition of increasing amounts of B(OPh)(3), the rate of the reaction of the imine complexed with the chiral catalyst must be at least 10 times faster than the reaction of the imine complexed with B(OPh)(3). Finally, a catalyst generated from BINOL and B(OPh)(3) does not show this phenomenon.
• Non-linear effects operate and dynamic ligand exchange occurs when chiral BINOL–boron Lewis acids are used for asymmetric catalysis
  作者：Jean Philippe Cros、Yolanda Pérez-Fuertes、Michael J Thatcher、Susumu Arimori、Steven D Bull、Tony D James

  DOI：10.1016/s0957-4166(03)00352-5

  日期：2003.7

  Non-linear effects reveal that the use of chiral BINOL-boron reagents for aza-Diels-Alder reactions results in an enantioselective catalytic species containing at least 2 equiv. of BINOL. Dynamic ligand exchange and ligand accelerated catalysis occurs in these reactions, consistent with the formation of a cyclic borate ester of BINOL with enhanced Lewis acidity. (C) 2003 Elsevier Science Ltd. All rights reserved.