(R)-1,2-epoxy-3-(3-methylphenoxy)propane | 56715-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1,2-epoxy-3-(3-methylphenoxy)propane
• 英文别名: 1,2-epoxy-3-(3-methylphenoxy)propane；(R)-(-)-m-tolyl glycidyl ether；(2R)-2-[(3-methylphenoxy)methyl]oxirane
• CAS: 56715-31-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: WYAFQPYCJBLWAS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯乙胺 、 (R)-1,2-epoxy-3-(3-methylphenoxy)propane 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 (R)-盐酸贝伐洛尔
  参考文献：
  名称：

  The effective direct resolution procedure for the chiral drug bevantolol hydrochloride

  摘要：

  The solubility of the chiral drug bevantolol hydrochloridel in water and the azeotropic mixture ethanol water has been investigated. It was found that rac-1 meets the requirements of Meyerhoffer's rule, so it was possible to reduce the ternary diagram, describing the solubility of 1, to a pseudo binary form, which facilitates the analysis of crystallization processes caused by temperature changes. On this basis, the effective and robust resolution procedure of racemic bevantolol hydrochloride by a preferential crystallization approach has been realized successfully. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.03.012
• 作为产物：
  描述：

  右旋环氧氯丙烷 、 间甲酚 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (R)-1,2-epoxy-3-(3-methylphenoxy)propane
  参考文献：
  名称：

  The effective direct resolution procedure for the chiral drug bevantolol hydrochloride

  摘要：

  The solubility of the chiral drug bevantolol hydrochloridel in water and the azeotropic mixture ethanol water has been investigated. It was found that rac-1 meets the requirements of Meyerhoffer's rule, so it was possible to reduce the ternary diagram, describing the solubility of 1, to a pseudo binary form, which facilitates the analysis of crystallization processes caused by temperature changes. On this basis, the effective and robust resolution procedure of racemic bevantolol hydrochloride by a preferential crystallization approach has been realized successfully. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.03.012

文献信息

• An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
  作者：Jing Zhao、Yan-Yan Chu、Ai-Tao Li、Xin Ju、Xu-Dong Kong、Jiang Pan、Yun Tang、Jian-He Xu

  DOI：10.1002/adsc.201100031

  日期：2011.6

  ortho‐substituted phenyl glycidyl ethers and para‐nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)‐enantiopreference was unexpectedly observed for the ortho‐nitrophenyl glycidyl ether. As a proof‐of‐concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram‐scale preparation of

  从巨大芽孢杆菌ECU1001中克隆了一种新的环氧水解酶（BMEH），该酶具有异常的（R）-对映体选择性和很高的活性。在对位取代的苯基缩水甘油醚和对硝基苯乙烯氧化物的生物拆分中，实现了最高的对映选择性（E > 200）。值得一提的是，底物结构显着影响了酶的对映选择性，因为人们意外地观察到邻硝基硝基苯缩水甘油醚的反向（S）-对映体选择性。作为概念验证，以高收率获得了五种对映纯环氧化合物（> 99％ee），并以克级制备了（S） -邻甲基苯基缩水甘油基醚，然后成功地在几个小时内完成，这表明BMEH为光学活性的环氧化物的高效制备有吸引力的生物催化剂。
• 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 )
• Stereoselective Hydrolysis of Epoxides by re<i>Vr</i>EH3, a Novel <i>Vigna radiata</i> Epoxide Hydrolase with High Enantioselectivity or High and Complementary Regioselectivity
  作者：Die Hu、Cunduo Tang、Chuang Li、Tingting Kan、Xiaoling Shi、Lei Feng、Minchen Wu

  DOI：10.1021/acs.jafc.7b03804

  日期：2017.11.15

  for the stereoselective hydrolysis of epoxides, an epoxide hydrolase (VrEH3) gene from Vigna radiata was cloned and expressed in Escherichia coli. Recombinant VrEH3 displayed the maximum activity at pH 7.0 and 45 °C and high stability at pH 4.5–7.5 and 55 °C. Notably, reVrEH3 exhibited high and complementary regioselectivity toward styrene oxides 1a–3a and high enantioselectivity (E = 48.7) toward o-cresyl

  为了为环氧化物的立体选择性水解提供更多选择，克隆了来自Vigna radiata的环氧化物水解酶（Vr EH3）基因并在大肠杆菌中表达。重组Vr EH3在pH 7.0和45°C时显示出最大活性，在pH 4.5–7.5和55°C时显示出高稳定性。值得注意的是，re Vr EH3对苯乙烯氧化物1a - 3a具有较高的互补区域选择性，对邻甲酚基缩水甘油醚9a具有较高的对映选择性（E = 48.7）。为了阐明这些有趣的现象，Vr之间的三维结构相互作用通过分子对接模拟分析了EH3和1a和9a的对映异构体。使用大肠杆菌/ vreh3全细胞，（革兰氏规模的制备- [R ） - 1B和（- [R ）-图9a是由100毫水解对映进行外消旋- 1A和200mM的动力学拆分外消旋-图9a在缓冲器-自由25°C的水系统。这些在重结晶后提供（R）-1b，其ee p > 99％，总产率为78.7％，（R）-9a具有>
• 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。
• Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium
  作者：Feng Xue、Xiangju Ya、Yuansong Xiu、Qi Tong、Yuqi Wang、Xinhai Zhu、He Huang

  DOI：10.1007/s10562-019-02659-0

  日期：2019.2

  AbstractA gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20 mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99%

  摘要 鉴定、克隆并在大肠杆菌中过表达了编码来自α变形杆菌的卤代醇脱卤酶（AbHHDH）的基因。AbHHDH 能够催化前手性和外消旋卤代醇的立体选择性脱卤。它在 20 mM (R,S)-2-bromo-1-苯基乙醇的脱卤反应中表现出最高的对映选择性，生成 (S)-2-bromo-1-苯基乙醇，ee 为 99%，产率为 34.5%。此外，AbHHDH 以低至中等 (S)-对映选择性催化环氧化物的叠氮分解。当 (R,S)-苄基缩水甘油醚用作底物时，观察到最高的对映选择性 (E = 18.6)。由 HHDH 催化的连续动力学拆分用于合成手性 1-氯-3-苯氧基-2-丙醇。我们制备了对映纯 (S)-异构体，ee> 99% 的高对映纯度和 30 的产率。20 mM 底物的动力学分辨率为 7%（E 值：21.3）。从 40 到 150 mM (R,S)-1-chloro-3-phenoxy-2-propanol