(S)-(4-tert-butylphenyl)(pyridin-2-yl)methanol | 1375005-46-1

• 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: (S)-(4-tert-butylphenyl)(pyridin-2-yl)methanol
• 英文别名: (S)-(4-tert-butylphenyl)-pyridin-2-ylmethanol
• CAS: 1375005-46-1
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: RQPIJFCZAQECEM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴吡啶 、 对叔丁基苯甲醛 在 正丁基锂 、 正丁基氯化镁 、 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (S)-(4-tert-butylphenyl)(pyridin-2-yl)methanol 、 (R)-(4-tert-butylphenyl)(pyridin-2-yl)methanol
  参考文献：
  名称：

  Pyridylmagnesiates: generation by bromine–metal exchange and enantioselective addition to aldehydes

  摘要：

  Butyl and dibutylmagnesiates incorporating chiral ligands have been prepared and their reactivity studied. The reagents were efficient to promote the clean bromine-magnesium exchange of azinyl bromides at room temperature and subsequent reaction with aldehydes affording pyridylcarbinols. (R,R)-TADDOL-based dibutylmagnesiate was the best reagent leading to acceptable to good enantioselectivities, depending on the substrate and on the aldehyde substitution. This is the first example of enantioselective addition of in situ generated pyridylmagnesiate to carbonyl electrophiles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.058

文献信息

• Pyridylmagnesiates: generation by bromine–metal exchange and enantioselective addition to aldehydes
  作者：Delphine Catel、Olivier Payen、Floris Chevallier、Florence Mongin、Philippe C. Gros

  DOI：10.1016/j.tet.2012.03.058

  日期：2012.5

  Butyl and dibutylmagnesiates incorporating chiral ligands have been prepared and their reactivity studied. The reagents were efficient to promote the clean bromine-magnesium exchange of azinyl bromides at room temperature and subsequent reaction with aldehydes affording pyridylcarbinols. (R,R)-TADDOL-based dibutylmagnesiate was the best reagent leading to acceptable to good enantioselectivities, depending on the substrate and on the aldehyde substitution. This is the first example of enantioselective addition of in situ generated pyridylmagnesiate to carbonyl electrophiles. (C) 2012 Elsevier Ltd. All rights reserved.