E-3-(N-benzoylpiperidin-4-yl)-1-phenylprop-1-ene | 189109-40-8

• 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: E-3-(N-benzoylpiperidin-4-yl)-1-phenylprop-1-ene
• 英文别名: phenyl-[4-[(E)-3-phenylprop-2-enyl]piperidin-1-yl]methanone
• CAS: 189109-40-8
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: FZOUMKMDICEEKZ-JXMROGBWSA-N

物化性质

• 沸点：
  471.5±14.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  E-3-(N-benzoylpiperidin-4-yl)-1-phenylprop-1-ene 在 原乙酸三甲酯 、 AD-mix-α 、 三甲基氯硅烷 、 甲基磺酰胺 、 甲基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 xylene 、 叔丁醇 为溶剂， 生成 (2R,1'S)-2-(1-hydroxy-1-phenyl)methyl-1-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine

  摘要：

  An enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine is reported. Key steps involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to form the quinuclidine ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00310-9
• 作为产物：
  描述：

  4-哌啶乙醇 在 sodium hydroxide 、 草酰氯 、 碘 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 E-3-(N-benzoylpiperidin-4-yl)-1-phenylprop-1-ene
  参考文献：
  名称：

  Enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine

  摘要：

  An enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine is reported. Key steps involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to form the quinuclidine ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00310-9

文献信息

• Enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine
  作者：Barry Lygo、John Crosby、Terence R. Lowdon、Philip G. Wainwright

  DOI：10.1016/s0040-4039(97)00310-9

  日期：1997.3

  An enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine is reported. Key steps involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to form the quinuclidine ring. (C) 1997 Elsevier Science Ltd.
• Asymmetric approaches to 2-hydroxymethylquinuclidine derivatives
  作者：B. Lygo、J. Crosby、T. Lowdon、P.G. Wainwright

  DOI：10.1016/s0040-4020(99)00050-2

  日期：1999.2

  Highly enantio- and diastereoselective routes to 2-hydroxymethylquinuclidines have been developed. Key steps involve the use of Sharpless dihydroxylation or Sharpless epoxidation to introduce the asymmetry with high stereocontrol, and formation of the quinuclidine ring systems via cyclisation of epoxy amines. (C) 1999 Elsevier Science Ltd. All rights reserved.