(2R)-3-甲苯氧基-1,2-环氧丙烷 | 206126-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2R)-3-甲苯氧基-1,2-环氧丙烷
• 英文名称: 1,2-epoxy-3-(2-methylphenoxy)propane
• 英文别名: (2R)-3-tolyloxy-1,2-epoxypropane；(R)-Glycidyl O-methylphenyl ether；(2R)-2-[(2-methylphenoxy)methyl]oxirane
• CAS: 206126-37-6
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: KFUSXMDYOPXKKT-SECBINFHSA-N

物化性质

• 沸点：
  65-68 °C(Press: 0.05 Torr)
• 密度：
  1.094±0.06 g/cm3(Predicted)

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：

  伊伐布雷定杂质2 、 (2R)-3-甲苯氧基-1,2-环氧丙烷 以 异丙醇 为溶剂， 反应 24.0h， 生成 3-{3-[((R)-2-Hydroxy-3-o-tolyloxy-propyl)-methyl-amino]-propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one
  参考文献：
  名称：

  Cardiovascular hybrid drugs: new benzazepinone derivatives as bradycardic agents endowed with selective β 1 -Non-competitive antagonism

  摘要：

  The synthesis and pharmacological profile of some hybrid compounds bearing both the benzazepinone moiety present in Zatebradine and typical P-blocker aryloxypropanolamine groups are described. The new compounds proved to be endowed with negative chronotropic and inotropic activity and are weak vasorelaxant agents. The cardiodepressant action is probably due to selective beta(1)-noncompetitive reversible antagonism. Both enantiomers of the most active compound 5c were synthesized and they showed a different cardiovascular profile, that is (+)-(R)-enantiomer displays affinity for cardiac beta(1)-adrenoceptors, while (-)-(S)-enantiomer shows specificity for vessel smooth muscle. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00621-1
• 作为产物：
  描述：

  (R)-(+)-3-(2-methylphenoxy)propane-1,2-diol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 (2R)-3-甲苯氧基-1,2-环氧丙烷
  参考文献：
  名称：

  Cardiovascular hybrid drugs: new benzazepinone derivatives as bradycardic agents endowed with selective β 1 -Non-competitive antagonism

  摘要：

  The synthesis and pharmacological profile of some hybrid compounds bearing both the benzazepinone moiety present in Zatebradine and typical P-blocker aryloxypropanolamine groups are described. The new compounds proved to be endowed with negative chronotropic and inotropic activity and are weak vasorelaxant agents. The cardiodepressant action is probably due to selective beta(1)-noncompetitive reversible antagonism. Both enantiomers of the most active compound 5c were synthesized and they showed a different cardiovascular profile, that is (+)-(R)-enantiomer displays affinity for cardiac beta(1)-adrenoceptors, while (-)-(S)-enantiomer shows specificity for vessel smooth muscle. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00621-1

文献信息

• Enantioselective α-hydroxylation of β-keto esters catalyzed by chiral S-timolol derivatives
  作者：Yuanchun Cai、Mingming Lian、Zhi Li、Qingwei Meng

  DOI：10.1016/j.tet.2012.07.003

  日期：2012.9

  derived from the β-blocker inhibitor S-timolol determined the most active catalyst of asymmetric α-hydroxylation of β-keto esters. (R)-1-(tert-butylamino)-3-(3,4,5-trimethoxyphenoxy) propan-2-ol (3k) was the most effective derivative, enantioselectively catalyzing α-hydroxylation of β-keto esters using tert-butyl hydroperoxide as the oxidant in hexane to afford the corresponding products in excellent yield

  由β-阻滞剂抑制剂S-噻吗洛尔衍生的芳氧基氨基丙醇有机催化剂的筛选确定了β-酮酯的不对称α-羟基化的最具活性的催化剂。（R）-1-（叔丁基氨基）-3-（3,4,5-三甲氧基苯氧基）丙烷-2-醇（3k）是最有效的衍生物，它使用叔-对映体催化β-酮酸酯的α-羟基化。丁基过氧化氢作为己烷中的氧化剂，以优异的收率和良好的对映选择性（高达96％的收率，88％ee）提供相应的产物。
• Novel lapachone compounds and methods of use thereof
  申请人：Ashwell Mark A.

  公开号：US20090105166A1

  公开（公告）日：2009-04-23

  The present invention provides novel tricyclic spiro-oxathiine naphthoquinone derivatives, a synthetic method for making the derivatives, and the use of the derivatives to induce cell death and/or to inhibit proliferation of cancer or precancerous cells. The naphthoquinone derivatives of the present invention are related to the compound known as β-lapachone (3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione).

  本发明提供了一种新型的三环螺-氧杂硫杂萘醌衍生物，一种制造该衍生物的方法，以及利用该衍生物诱导细胞死亡和/或抑制癌症或前癌细胞增殖的应用。本发明的萘醌衍生物与被称为β-拉帕醇（3,4-二氢-2,2-二甲基-2H-萘(1,2-b)吡喃-5,6-二酮）的化合物有关。
• 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>
• Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes
  作者：Rajkumar Tak、Manish Kumar、Tusharkumar Menapara、Naveen Gupta、Rukhsana I. Kureshy、Noor-ul H. Khan、E. Suresh

  DOI：10.1002/adsc.201700788

  日期：2017.11.23

  New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric

  合成了新的手性大环钴（III）salen络合物，并用作端环氧化物和缩水甘油醚与芳香族/脂肪族胺和水为亲核试剂的不对称动力学拆分（AKR）的催化剂。这是Co（III）salen配合物首次证明其催化AKR以及水解动力学拆分（HKR）反应的能力。通过在室温下在二氯甲烷中使用手性Co（III）salen络合物，可实现定量的优异环氧化物，相应的氨基醇和二醇（至多99％）的出色的对映异构体过量。该方案进一步扩展为合成两个重要的药物分子，即（S）-普萘洛尔和（R）-萘哌地尔。还探索了使用二氧化碳作为绿色可再生C 1来源合成手性纯二醇和手性环状碳酸酯的催化体系。在保持对映选择性的情况下，将催化剂循环使用多达5个催化循环。