(1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediol | 924637-68-3

• 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: (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediol
• 英文别名: (1RS,2RS,3RS)-2-Methyl-1-phenylbutan-1,3-diol；(1S,2S,3S)-2-methyl-1-phenylbutane-1,3-diol
• CAS: 924637-68-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: QHXAOJQLZHLLON-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-1-苯基-1,3-丁二酮 在 sodium tetrahydroborate 、 葡萄糖 、 Zygosaccharomyces rouxii 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediol
  参考文献：
  名称：

  A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms

  摘要：

  Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (IR,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1, 3-butanedione, both involving in situ racemization. The first method comprised a one-pot microbial reduction coupled with a chemical reduction, while in the second method, stepwise chemo-enzymatic reductions were performed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.045

文献信息

• Baker's Yeast Reduction of β-Hydroxy Ketones
  作者：Daniela Acetti、Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Stefano Serra

  DOI：10.1002/ejoc.200901006

  日期：2010.1

  Reduction of β-hydroxy ketones to the corresponding 1,3-diols by baker's yeast was investigated, in order to develop methods for simultaneous control over the configurations of multiple stereogenic centres. The reactions were found to be enantiospecific and generally characterised by good diastereoselectivity. Substrates with a substituent at the carbon atom in the α position were also considered.

  研究了面包酵母将 β-羟基酮还原为相应的 1,3-二醇，以开发同时控制多个立体中心构型的方法。发现这些反应是对映特异性的，并且通常以良好的非对映选择性为特征。还考虑了在 α 位置的碳原子上具有取代基的底物。当α-碳原子上的取代基是环的一部分时，观察到更高的选择性。