(1'S)-2-[1'-(tert-butyldimethylsilyloxy)-2',2'-dimethylpropyl]-6-hydroxymethylpyridine | 353495-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1'S)-2-[1'-(tert-butyldimethylsilyloxy)-2',2'-dimethylpropyl]-6-hydroxymethylpyridine
• 英文别名: [6-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethylpropyl]pyridin-2-yl]methanol
• CAS: 353495-92-8
• 化学式: C₁₇H₃₁NO₂Si
• 分子量: 309.524
• InChiKey: AWKNWEYXRQFUBE-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S)-2-[1'-(tert-butyldimethylsilyloxy)-2',2'-dimethylpropyl]-6-hydroxymethylpyridine 在 盐酸 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 84.5h， 生成 (2'R,5'R,1''S)-2-[(2',5'-dimethylpyrrolidin-1-yl)methyl]-6-(1''-methoxy-2'',2''-dimethylpropyl)pyridine
  参考文献：
  名称：

  Pyrrolidinopyridines in Palladium-Catalyzed Allylic Substitutions − Conformation of the Ligand

  摘要：

  The (R,R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]pyridines 4, 5, and 6 carrying a 2-hydroxyalkyl, 2-alkoxyalkyl or 2-siloxyalkyl substituent in the 6-position of the pyridine ring were prepared and assessed in palladium-catalyzed allylations of 1,3-diphenylpropenyl acetate with malonate. All ligands having g-substituents with an S absolute configuration afforded the product with an R configuration in 80-84% ee, whereas those having substituents with an R absolute configuration gave the opposite product with a selectivity depending on the nature of the substituent (8-74% ee). It is believed that the enantioselectivity is dependent on the conformation of that substituent.

  DOI：

  10.1002/1099-0690(200106)2001:11<2191::aid-ejoc2191>3.0.co;2-x
• 作为产物：
  描述：

  (S)-1-(6-溴吡啶-2-基)-2,2-二甲基丙-1-醇 在 咪唑 、 正丁基锂 作用下， 以 various solvents 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.83h， 生成 (1'S)-2-[1'-(tert-butyldimethylsilyloxy)-2',2'-dimethylpropyl]-6-hydroxymethylpyridine
  参考文献：
  名称：

  Pyrrolidinopyridines in Palladium-Catalyzed Allylic Substitutions − Conformation of the Ligand

  摘要：

  The (R,R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]pyridines 4, 5, and 6 carrying a 2-hydroxyalkyl, 2-alkoxyalkyl or 2-siloxyalkyl substituent in the 6-position of the pyridine ring were prepared and assessed in palladium-catalyzed allylations of 1,3-diphenylpropenyl acetate with malonate. All ligands having g-substituents with an S absolute configuration afforded the product with an R configuration in 80-84% ee, whereas those having substituents with an R absolute configuration gave the opposite product with a selectivity depending on the nature of the substituent (8-74% ee). It is believed that the enantioselectivity is dependent on the conformation of that substituent.

  DOI：

  10.1002/1099-0690(200106)2001:11<2191::aid-ejoc2191>3.0.co;2-x

文献信息

• Pyrrolidinopyridines in Palladium-Catalyzed Allylic Substitutions − Conformation of the Ligand
  作者：Robert Stranne、Christina Moberg

  DOI：10.1002/1099-0690(200106)2001:11<2191::aid-ejoc2191>3.0.co;2-x

  日期：2001.6

  The (R,R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]pyridines 4, 5, and 6 carrying a 2-hydroxyalkyl, 2-alkoxyalkyl or 2-siloxyalkyl substituent in the 6-position of the pyridine ring were prepared and assessed in palladium-catalyzed allylations of 1,3-diphenylpropenyl acetate with malonate. All ligands having g-substituents with an S absolute configuration afforded the product with an R configuration in 80-84% ee, whereas those having substituents with an R absolute configuration gave the opposite product with a selectivity depending on the nature of the substituent (8-74% ee). It is believed that the enantioselectivity is dependent on the conformation of that substituent.