(S)-4-methyl-2-(1-phenylethyl)phenol

• 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-methyl-2-(1-phenylethyl)phenol
• 英文别名: 4-methyl-2-((S)-1-phenyl-ethyl)-phenol；4-Methyl-2-((S)-1-phenyl-aethyl)-phenol；4-methyl-2-[(1S)-1-phenylethyl]phenol
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: DJRYJQNZAYJVGF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-2-(1-苯基乙烯基)苯酚 在 Rh(COD)[(R,S)-DuanPhos]BF₄ 、 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99%的产率得到(S)-4-methyl-2-(1-phenylethyl)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

• Notes - Stereochemical Control by Solvent in the Thermal Rearrangement of Aryl α-Phenethyl Ethers
  作者：Harold Hart、John Kosak

  DOI：10.1021/jo01106a623

  日期：1958.12
• The Stereochemistry of Aromatic Alkylations. II. The Thermal Rearrangement of Alkyl Aryl Ethers¹
  作者：Harold Hart、Herbert S. Eleuterio

  DOI：10.1021/ja01631a055

  日期：1954.1
• 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.