2-(5,5-dimethylcyclopent-1-enyl)phenol | 1275593-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(5,5-dimethylcyclopent-1-enyl)phenol
• 英文别名: 2-(5,5-Dimethylcyclopenten-1-yl)phenol
• CAS: 1275593-40-2
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: PFRQQHCXPMRUDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(5,5-dimethylcyclopent-1-enyl)phenol 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 Josiphos SL-J-210-1 、 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 以93%的产率得到2-(2,2-dimethylcyclopentyl)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