(S)-(-)-2',2',1'-triphenyl-2-hydroxyethyl-(S)-3-hydroxy-1-azabicyclo[2.2.2]octane-3-acetate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-(-)-2',2',1'-triphenyl-2-hydroxyethyl-(S)-3-hydroxy-1-azabicyclo[2.2.2]octane-3-acetate
• 英文别名: [(1S)-2-hydroxy-1,2,2-triphenylethyl] 2-[(3S)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]acetate
• 化学式: C₂₉H₃₁NO₄
• 分子量: 457.569
• InChiKey: XXAFKXCAJJEONO-WUFINQPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2',2',1'-triphenyl-2-hydroxyethyl-(S)-3-hydroxy-1-azabicyclo[2.2.2]octane-3-acetate 在 potassium cyanide 、 肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 ((R)-3-Hydroxy-1-aza-bicyclo[2.2.2]oct-3-yl)-acetic acid hydrazide
  参考文献：
  名称：

  A Chiral Synthesis of (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘- oxazolidin-2‘-one]:  A Conformationally Restricted Analogue of Acetylcholine That Is a Potent and Selective α7 Nicotinic Receptor Agonist

  摘要：

  A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.

  DOI：

  10.1021/jo049404q
• 作为产物：
  描述：

  3-奎宁环酮 、 (S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 以51%的产率得到(S)-(-)-2',2',1'-triphenyl-2-hydroxyethyl-(S)-3-hydroxy-1-azabicyclo[2.2.2]octane-3-acetate
  参考文献：
  名称：

  A Chiral Synthesis of (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘- oxazolidin-2‘-one]:  A Conformationally Restricted Analogue of Acetylcholine That Is a Potent and Selective α7 Nicotinic Receptor Agonist

  摘要：

  A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.

  DOI：

  10.1021/jo049404q

文献信息

• A Chiral Synthesis of (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘- oxazolidin-2‘-one]:  A Conformationally Restricted Analogue of Acetylcholine That Is a Potent and Selective α7 Nicotinic Receptor Agonist
  作者：John E. Macor、George Mullen、Patrick Verhoest、Anthony Sampognaro、Bruce Shepardson、Robert A. Mack

  DOI：10.1021/jo049404q

  日期：2004.9.1

  A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.