(R)-3-(4-methylphenoxy)-propane-1,2-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-(4-methylphenoxy)-propane-1,2-diol
• 英文别名: (R)-3-(4-methylphenoxy)propane-1,2-diol；(R)-3-(p-methylphenoxy)-1,2-propanediol；(R)-3-(p-tolyloxy)propane-1,2-diol；(2R)-3-(4-methylphenoxy)propane-1,2-diol
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: HEILYJUNOUXHJQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-acetoxy-3-(4-methylphenoxy)propan-2-ol 在 baker's yeast 、 草酰氯 、 sodium phosphate buffer 、 二甲基亚砜 、 三乙胺 、 蔗糖 作用下， 反应 2.83h， 生成 (R)-3-(4-methylphenoxy)-propane-1,2-diol
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5

文献信息

• Highly regio- and enantio-selective hydrolysis of two racemic epoxides by GmEH3, a novel epoxide hydrolase from Glycine max
  作者：Chen Zhang、Chuang Li、Xiu-xiu Zhu、You-yi Liu、Jun Zhao、Min-chen Wu

  DOI：10.1016/j.ijbiomac.2020.08.011

  日期：2020.12

  50 mM−1 s−1) of purified GmEH3 for (S)-5a was slightly higher than that (kcatR/KmR = 1.52 mM−1 s−1) for (R)-5a, whereas the kcat/Km (5.16 mM−1 s−1) for (S)-7a was much higher than that (0.09 mM−1 s−1) for (R)-7a. Using 200 mg/mL wet cells of E. coli/gmeh3 as the biocatalyst, the scale-up enantioconvergent hydrolysis of 150 mM rac-5a at 25 °C for 1.5 h afforded (R)-5b with 90.2% eep and 95.4% yieldp

  基于计算机辅助分析，从大豆中挖掘出一种新型环氧化物水解酶，命名为Gm EH3。然后，克隆了Gm EH3编码基因gmeh3 ，并在大肠杆菌Rosetta(DE3)中成功表达。在所研究的十种外消旋环氧化物中， Gm EH3 在外消旋间氯苯乙烯氧化物 ( 5a ) 的不对称水解中具有最高和最好的互补区域选择性（区域选择性系数， α S = 93.7% 和 β R = 97.2%），并且对外消旋苯基缩水甘油醚 ( 7a ) 具有最高的对映选择性（对映体比率， E = 55.6）。纯化的Gm EH3 对 ( S )- 5a的催化效率 ( k cat S / K m S = 2.50 mM -1 s -1 ) 略高于 ( k cat R / K m R = 1.52 mM -1 s - ) 1 ) ( R )- 5a ，而 ( S )- 7a的k cat / K m (5.16 mM −1 s −1 )
• Synthesis of<i>C</i>₂-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring
  作者：Yilmaz Turgut、Tarik Aral、Mehmet Karakaplan、Pinar Deniz、Halil Hosgoren

  DOI：10.1080/00397910903419878

  日期：2010.10.20

  A series of β-amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%).

  以(R)-2-氨基-1-丁醇和(S)-1,2-丙二醇为原料合成了一系列β-氨基醇衍生物，并以良好的收率在环氧化物的外消旋开环中用作有机催化剂对映体过量（高达 97%）。
• Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers.³¹P NMR analysis of the enantiomeric composition of oxiranes
  作者：A. A. Bredikhin、E. I. Strunskaya、V. G. Novikova、N. M. Azancheev、D. R. Sharafutdinova、Z. A. Bredikhina

  DOI：10.1023/b:rucb.0000024851.29744.21

  日期：2004.1

  The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2-dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously

  研究了在手性 Co(salen) 催化剂存在下，许多外消旋芳基缩水甘油醚的对映选择性部分水解。分离的(R)-芳基缩水甘油醚的对映体组成通过31P NMR使用光学活性取代的2-氯-1,3,2-二氧杂环戊烷进行分析。提出了基于同时获得的 (S)-3-芳氧基丙烷-1,2-二醇合成 β-肾上腺素阻滞剂 (S)-toliprolol 和 (S)-moprolol。
• Chiral Nanoporous Metal–Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides
  作者：Chengfeng Zhu、Guozan Yuan、Xu Chen、Zhiwei Yang、Yong Cui

  DOI：10.1021/ja302340b

  日期：2012.5.16

  recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios

  手性纳米多孔金属有机框架是通过使用二羧基功能化的手性 Ni(salen) 和 Co(salen) 配体构建的。基于 Co(salen) 的框架被证明是一种高效且可回收的多相催化剂，用于外消旋环氧化物的水解动力学拆分 (HKR)，ee 高达 99.5%。MOF 结构使 Co(salen) 单元形成高度密集的排列和紧密接近，增强了双金属协同相互作用，与均相类似物相比，HKR 的催化活性和对映选择性提高，尤其是在低催化剂/底物比的情况​​下。
• Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols
  作者：Tarik Aral、Mehmet Karakaplan、Halil Hoşgören

  DOI：10.1007/s10562-012-0814-4

  日期：2012.6

  A series of novel chiral β-amino alcohols 3–5 and 7–10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5,8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and

  通过环氧化物和手性胺的区域选择性开环，以高产率（高达 99%）的简单方法合成了一系列新型手性 β-氨基醇 3-5 和 7-10。通过使用手性氨基醇作为有机催化剂实现了外消旋缩水甘油与酚的动力学拆分。氨基醇 5,8 和 10 与对甲酚、苯酚和对甲氧基苯酚的对映选择性最高，分别为 63%、65% 和 58% ee。使用催化剂 9b 观察到对所有亲核试剂（34-48% ee）的中等对映选择性。所需的3-芳氧基-1,2-二醇的ee值通过HPLC测定。这项研究为合成 β-受体阻滞剂和结构复杂的分子提供了一种有吸引力的工具。