erythro-2-(α-hydroxybenzyl)quinuclidine

• 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: erythro-2-(α-hydroxybenzyl)quinuclidine
• 英文别名: (R)-[(2S)-1-azabicyclo[2.2.2]octan-2-yl]-phenylmethanol
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: PWPTXBISWPQFLV-UONOGXRCSA-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：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 erythro-2-(α-hydroxybenzyl)quinuclidine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以58%的产率得到(2S,1'R,1'''R)-2-<1-<(2-methoxy-2-phenyl-3-trifluoro)propanoyloxy>-1-phenyl>methyl-1-azabicyclo<2.2.2>octane
  参考文献：
  名称：

  Asymmetric approaches to 2-hydroxymethylquinuclidine derivatives

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(99)00050-2
• 作为产物：
  描述：

  3-奎宁环酮盐酸盐 在 吡啶 、 甲基锂 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 47.33h， 生成 erythro-2-(α-hydroxybenzyl)quinuclidine
  参考文献：
  名称：

  Model studies of a conceptually new approach to the total synthesis of quinine

  摘要：

  DOI：

  10.1021/jo00201a006

文献信息

• Facile α-deprotonation–electrophilic substitution of quinuclidine and DABCO
  作者：Satinder V. Kessar、Paramjit Singh、Kamal N. Singh、Sandeep K. Singh

  DOI：10.1039/a905359j

  日期：——

  Deprotonation of BF3 complexes of quinuclidine or DABCO by Schlosser base and subsequent reaction with electrophiles affords α-substituted products in moderate to good yields.

  用Schlosser碱对奎尼克啶或DABCO的BF3络合物进行去质子化，然后与电亲体反应，得到中等到良好的α-取代产物。
• Mono- and diaryl-2-quinuclidinylcarbinols with local anesthetic and antiarrhythmic activity
  作者：P. H. Nelson、A. M. Strosberg、K. G. Untch

  DOI：10.1021/jm00176a014

  日期：1980.2

  The reaction between 2-carboethoxyquinuclidine and various aryl- and heteroarylithium reagents gave mixtures of aryl 2-quinuclidinyl ketones and diaryl-2-quinuclidinylcarbinols. Diborane reduction of the ketones gave the erythro-carbinols, stereochemically analogous to quinidine. Several of the mono- and diarylcarbinols exhibited potent local anesthetic and antiarrhythmic activity, in some cases greater

  2-羰基乙氧基奎宁环烷与各种芳基和杂芳基锂试剂之间的反应得到了芳基2-奎宁环烷基酮和二芳基-2-奎宁环烷基羰基的混合物。乙酮的乙硼烷还原生成立体异构类似于奎尼丁的赤藓醇。几种单和二芳基甲醇会表现出有效的局部麻醉和抗心律不齐活性，在某些情况下，其活性高于奎尼丁。二苯基-2-奎宁环戊基甲醇和（溴甲氧基苯基）（甲氧基苯基）-2-奎宁环基甲醇在犬哇巴因性心律失常的恢复中特别活跃，显示出等效于或大于普萘洛尔的作用力和作用时间。
• 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.
• Model studies of a conceptually new approach to the total synthesis of quinine
  作者：Philip L. Stotter、Martin D. Friedman、David E. Minter

  DOI：10.1021/jo00201a006

  日期：1985.1
• 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.