(2R,1'S)-2-(1-hydroxy-1-phenyl)methyl-1-azabicyclo[2.2.2]octane | 189177-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: (2R,1'S)-2-(1-hydroxy-1-phenyl)methyl-1-azabicyclo[2.2.2]octane
• 英文别名: (S)-[(2R)-1-azabicyclo[2.2.2]octan-2-yl]-phenylmethanol
• CAS: 189177-06-8
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: PWPTXBISWPQFLV-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,1'S)-2-(1-hydroxy-1-phenyl)methyl-1-azabicyclo[2.2.2]octane 在 rhodium on aluminium 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 170.0h， 生成 (2R,1'S)-2-(1-cyclohexyl-1-hydroxy)methyl-1-phenylmethyl-azoniabicyclo[2.2.2]octane
  参考文献：
  名称：

  Structure–selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters

  摘要：

  In this paper, we describe the synthesis of a series of chiral quaternary ammonium salts with core structures that are closely related to the cinchona alkaloid, cinchonine. By employing these salts as asymmetric phase-transfer agents in the benzylation of a glycine imine, an optimal catalyst structure is identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00093-x
• 作为产物：
  描述：

  4-哌啶乙醇 在 原乙酸三甲酯 、 sodium hydroxide 、 AD-mix-α 、 三甲基氯硅烷 、 草酰氯 、 甲基磺酰胺 、 甲基锂 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 、 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

文献信息

• 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.
• Structure–selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters
  作者：B. Lygo、J. Crosby、T.R. Lowdon、P.G. Wainwright

  DOI：10.1016/s0040-4020(01)00093-x

  日期：2001.3

  In this paper, we describe the synthesis of a series of chiral quaternary ammonium salts with core structures that are closely related to the cinchona alkaloid, cinchonine. By employing these salts as asymmetric phase-transfer agents in the benzylation of a glycine imine, an optimal catalyst structure is identified. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.