rac-2-(2-methoxy-5-methylphenyl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-2-(2-methoxy-5-methylphenyl)propan-1-ol
• 英文别名: 2-(2-Hydroxy-1-methyl-ethyl)-4-methyl-anisol；2-(2-Methoxy-5-methylphenyl)propan-1-ol
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: UTENOUDMKJXJCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酸乙烯酯 、 rac-2-(2-methoxy-5-methylphenyl)propan-1-ol 在 Pseudomonas cepacia lipase 作用下， 以 正己烷 为溶剂， 反应 48.0h， 以0.2 g的产率得到(+)-2-(2-methoxy-5-methylphenyl)propan-1-ol
  参考文献：
  名称：

  Lipase catalyzed kinetic resolution of rac-2-phenylpropan-1-ol derivatives as building block for phenolic sesquiterpenes

  摘要：

  Highly enantioselective and enantiospecific resolution processes were developed for 2-(3-methoxy-4-methyl-phenyl)-propan-1-ol (VI), 2-(2-methoxy-5-methyl-phenyl)-propan-1-ol (VII), 2-(3,4,5-trimethoxy-phenyl)-propan-1-ol (VIII) and 2-(3-hydroxy-4-methyl-phenyl)-propan-1-ol (XII) via lipase-catalyzed transesterification and hydrolysis using vinyl propionate as acylating agent. The general procedure for synthesis and kinetic resolution of 2-phenylpropan-1-ol derivatives would be beneficial for getting chiral building block of bisabolane types of natural and unnatural sesquiterpenes. Gallic acid moiety was diversified with a chiral center at the benzylic position and subsequent resolution process gave resolved isomers with higher enantiopurity. Both isomers were separated with ee of at least 95%. Enantioselectivity, E was even higher up to 316 during the process. These resolved chiral intermediates will facilitate the commercial synthesis of bio-active natural and unnatural xanthorrhizol, elvirol and gallate derivatives. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.10.005
• 作为产物：
  描述：

  2-(2-Hydroxy-5-methyl-phenyl)-propanol-(1) 、 硫酸二甲酯 生成 rac-2-(2-methoxy-5-methylphenyl)propan-1-ol
  参考文献：
  名称：

  Alkylation of phenols with mixed-functional compounds

  摘要：

  DOI：

  10.1007/bf00906150

文献信息

• Lipase catalyzed kinetic resolution of rac-2-phenylpropan-1-ol derivatives as building block for phenolic sesquiterpenes
  作者：Azam Sharif Mohammed Shafioul、Chan Seong Cheong

  DOI：10.1016/j.molcatb.2011.10.005

  日期：2012.2

  Highly enantioselective and enantiospecific resolution processes were developed for 2-(3-methoxy-4-methyl-phenyl)-propan-1-ol (VI), 2-(2-methoxy-5-methyl-phenyl)-propan-1-ol (VII), 2-(3,4,5-trimethoxy-phenyl)-propan-1-ol (VIII) and 2-(3-hydroxy-4-methyl-phenyl)-propan-1-ol (XII) via lipase-catalyzed transesterification and hydrolysis using vinyl propionate as acylating agent. The general procedure for synthesis and kinetic resolution of 2-phenylpropan-1-ol derivatives would be beneficial for getting chiral building block of bisabolane types of natural and unnatural sesquiterpenes. Gallic acid moiety was diversified with a chiral center at the benzylic position and subsequent resolution process gave resolved isomers with higher enantiopurity. Both isomers were separated with ee of at least 95%. Enantioselectivity, E was even higher up to 316 during the process. These resolved chiral intermediates will facilitate the commercial synthesis of bio-active natural and unnatural xanthorrhizol, elvirol and gallate derivatives. (C) 2011 Elsevier B.V. All rights reserved.
• Alkylation of phenols with mixed-functional compounds
  作者：N. I. Shuikin、E. A. Viktorova、I. E. Pokrovskaya、T. G. Malysheva

  DOI：10.1007/bf00906150

  日期：1961.9