(S)-2-(1-(pyridin-3-yl)ethyl)phenol | 1275593-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-2-(1-(pyridin-3-yl)ethyl)phenol
• 英文别名: 2-[(1S)-1-pyridin-3-ylethyl]phenol
• CAS: 1275593-47-9
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: RGLWCQOAWBJXRY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  3-乙酰基吡啶 在 正丁基锂 、 Rh(COD)[(R,S)-DuanPhos]BF₄ 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 正己烷 、 甲苯 为溶剂， -78.0~60.0 ℃ 、344.75 kPa 条件下， 反应 7.5h， 生成 (S)-2-(1-(pyridin-3-yl)ethyl)phenol
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p

文献信息

• Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups
  作者：Xiang Wang、Anil Guram、Seb Caille、Jack Hu、J P. Preston、Michael Ronk、Shawn Walker

  DOI：10.1021/ol200422p

  日期：2011.4.1

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.