(R)-1,2-epoxy-3-(2-ethylphenoxy)propane | 1616790-43-2

• 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-(2-ethylphenoxy)propane
• 英文别名: 1-(2′-ethylphenoxy)-2,3-epoxy-propane；(2R)-2-[(2-ethylphenoxy)methyl]oxirane
• CAS: 1616790-43-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KSIFCIGYWZLLRY-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (R)-1,2-epoxy-3-(2-ethylphenoxy)propane 、 (R)-(-)-1,2,3,4-四氢-1-萘胺 以 乙醇 为溶剂， 反应 15.0h， 以74.7%的产率得到3-(2-ethylphenoxy)-1[(1R)-1,2,3,4-tetrahydronaphth-1-ylamino]-(2R)-2-propanol
  参考文献：
  名称：

  Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol

  摘要：

  Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epoxy-3-(2-ethylphenoxy)propanes (S)- and (R)-5 and then into non-racemic 3-(2-ethylphenoxy)-1(1,2,3,4-tetrahydronaphth-1-ylamino)-2-propanols 1. The characteristics of all four stereoisomers, (S,S)-1 (SR 59230), (R,R)-1 (SR 59483), (R,S)-1 and (S,R)-1 (SR 59231) and their hydrogen oxalates with a 1:1 composition have been presented. The crystalline oxalates (S,S)-1 center dot C2H2O4 (SR 59230A) and (R,S)-1 center dot 0.5C(2)H(2)O(4) were studied by single crystal X-ray diffraction. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.001
• 作为产物：
  描述：

  乙基苯酚 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (R)-1,2-epoxy-3-(2-ethylphenoxy)propane
  参考文献：
  名称：

  Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol

  摘要：

  Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epoxy-3-(2-ethylphenoxy)propanes (S)- and (R)-5 and then into non-racemic 3-(2-ethylphenoxy)-1(1,2,3,4-tetrahydronaphth-1-ylamino)-2-propanols 1. The characteristics of all four stereoisomers, (S,S)-1 (SR 59230), (R,R)-1 (SR 59483), (R,S)-1 and (S,R)-1 (SR 59231) and their hydrogen oxalates with a 1:1 composition have been presented. The crystalline oxalates (S,S)-1 center dot C2H2O4 (SR 59230A) and (R,S)-1 center dot 0.5C(2)H(2)O(4) were studied by single crystal X-ray diffraction. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.001

文献信息

• 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
• A Smart Library of Epoxide Hydrolase Variants and the Top Hits for Synthesis of (<i>S</i>)-β-Blocker Precursors
  作者：Xu-Dong Kong、Qian Ma、Jiahai Zhou、Bu-Bing Zeng、Jian-He Xu

  DOI：10.1002/anie.201402653

  日期：2014.6.23

  the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β‐blocker precursors. Improved activities of 6‐ to 430‐fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward

  酶活性口袋的微调已形成了环氧水解酶变体的智能库，其底物光谱范围扩大，涵盖了一系列典型的β-受体阻滞剂前体。通过在两个预计的热点上重新设计活动站点，可以将活动提高6到430倍。这项研究代表了环氧化物水解酶蛋白质工程的一项突破，并提高了对庞大底物的活性。
• Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol
  作者：Zemfira A. Bredikhina、Alexey V. Kurenkov、Dmitry B. Krivolapov、Alexander A. Bredikhin

  DOI：10.1016/j.tetasy.2016.05.001

  日期：2016.7

  Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epoxy-3-(2-ethylphenoxy)propanes (S)- and (R)-5 and then into non-racemic 3-(2-ethylphenoxy)-1(1,2,3,4-tetrahydronaphth-1-ylamino)-2-propanols 1. The characteristics of all four stereoisomers, (S,S)-1 (SR 59230), (R,R)-1 (SR 59483), (R,S)-1 and (S,R)-1 (SR 59231) and their hydrogen oxalates with a 1:1 composition have been presented. The crystalline oxalates (S,S)-1 center dot C2H2O4 (SR 59230A) and (R,S)-1 center dot 0.5C(2)H(2)O(4) were studied by single crystal X-ray diffraction. (C) 2016 Elsevier Ltd. All rights reserved.