ethyl (R)-2-(4-methoxyphenoxy)propanoate | 640997-22-4

• 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: ethyl (R)-2-(4-methoxyphenoxy)propanoate
• 英文别名: ethyl (2R)-2-(4-methoxyphenoxy)propanoate
• CAS: 640997-22-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: ZGFMBUHREWMBOI-SECBINFHSA-N

物化性质

• 沸点：
  307.6±17.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-(4-methoxyphenoxy)propanoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 methanesulfonic acid 2-(4-methoxy-phenoxy)-propyl ester
  参考文献：
  名称：

  Synthesis, conformation analysis and catalytic properties of chiral zirconium complexes containing etherfunctionalized Cp ligands

  摘要：

  A novel series of chiral ligands was synthesized having a cyclopentadienyl (Cp) ring attached to an ether moiety. Four chiral monoCp zirconium derivatives contain these ligands in a bidentate Cp/O coordination mode. Complexes 4d, 6d, and 7d bear an aryl group at the end of the ether chain. The racemic complexes 3d and 4d show moderate activity for the polymerisation of ethylene. Complexes 6d and 7d are enantiopure and were used as asymmetric Lewis acid catalysts for the hydrocyanation of benzaldehyde. The negligible enantiomeric excess thereby is due to decomplexation of the weakly coordinated aryl ether side-chains during catalysis. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00164-3
• 作为产物：
  描述：

  L(-)-乳酸乙酯 、 4-甲氧基苯酚 在 ethyl 2-(3,4-dichlorophenyl)azocarboxylate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以96%的产率得到ethyl (R)-2-(4-methoxyphenoxy)propanoate
  参考文献：
  名称：

  系统评价2-芳基羧酸酯和2-芳基甲酰胺作为Mitsunobu试剂

  摘要：

  2-芳基偶氮羧酸酯和2-芳基偶氮羧酰胺衍生物可以替代典型的Mitsunobu试剂，例如偶氮二羧酸二乙酯。对这些偶氮化合物的反应性和物理性质的系统研究表明，它们具有出色的Mitsunobu试剂能力。与已知的偶氮试剂相比，这些试剂显示出相似或更高的反应性，并且适用于广泛的底物范围。p ķ一已经研究了底物的空间效应和空间效应，并且可以通过从2-芳基偶氮羧酸酯和2-芳基偶氮甲酰胺衍生物的文库中选择合适的试剂来克服Mitsunobu反应的局限性。例如，通过一锅铁催化的好氧氧化可方便地回收偶氮试剂。代表性的2-芳基偶氮羧酸酯和2-芳基偶氮羧酰胺衍生物的SC-DSC分析显示出高的热稳定性，表明与典型的偶氮试剂相比，这些偶氮试剂具有较低的化学危害。

  DOI：

  10.1021/acs.joc.8b00486

文献信息

• Asymmetric Synthesis of Stagonolide-D and Stagonolide-G
  作者：Tridib Mahapatra、Tapas Das、Samik Nanda

  DOI：10.1246/bcsj.20100197

  日期：2011.5.15

  First asymmetric synthesis of the naturally occurring epoxy noneolide stagonolide-D has been reported in this article. Ring-closing metathesis (RCM) by Grubbs second generation catalyst, Sharpless asymmetric epoxidation (SAE), and cis-selective Horner–Wadsworth–Emmons (HWE) olefination by Ando method are the key reactions successfully employed to achieve the target molecule in a divergent approach. Structurally related small ring macrolide stagonolide-G has also been synthesized by employing RCM and a metal–enzyme combined dynamic kinetic resolution (DKR) strategy starting from (S)-ethyl lactate as a chiral pool.

  本文报道了天然环氧noneolide stagonolide-D的首次非对称合成。该合成通过使用第二代Grubbs催化剂的环合复分解（RCM）、Sharpless非对称环氧化（SAE）以及由Ando方法进行的顺式选择性Horner-Wadsworth-Emmons（HWE）烯化反应，成功地采用发散性途径合成了目标分子。从手性池来源的(S)-乳酸乙酯出发，利用RCM和金属-酶联合动态动力学拆分（DKR）策略，还合成了结构相关的小环大环内酯stagonolide-G。
• Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions
  作者：Shinji Kitagaki、Shunsuke Murata、Kisaki Asaoka、Kenta Sugisaka、Chisato Mukai、Naoko Takenaga、Keisuke Yoshida

  DOI：10.1248/cpb.c18-00519

  日期：2018.10.1

  insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2]paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular

  合成了直接连接到平面手性[2.2]对环环烷骨架上的中心手性双恶唑啉，并在Cu催化的α-重氮酯的分子间乙醇氢插入反应中将其作为不对称配体进行了评估。合成的双恶唑啉配体的Cu配合物的反应性和对映选择性低于没有中心手性的配体。然而，具有手性要求高的异丙基取代基的带有插入的苯间隔基的平面手性[2.2]对环环烷基双恶唑啉配体在分子间和分子内芳族OH插入反应中没有良好的对映选择性，而没有中心手性。
• [EN] A PROCESS FOR OPTICAL PURE (R)-2-PHENOXYPROPIONIC ACID DERIVATIVES<br/>[FR] PROCEDE DE FABRICATION DE DERIVES D'ACIDE (R)-2-PHENOXYPROPIONIQUE PURS OPTIQUEMENT ACTIFS
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2006001562A1

  公开（公告）日：2006-01-05

  The present invention relates to a method for manufacturing optically active (R)-2-phenoxypropionic acid derivatives. More particularly, the present invention relates to a method for manufacturing optically active (R)-2-phenoxypropionic acid derivatives with high purity by using p-substituted phenol derivatives and alkyl (S)-2-arylsulfonyloxypropionate as starting materials and reacting them at 60 to 100 °C in the presence of an alkalimetal salt as a base and. a hydrocarbon solvent.

  本发明涉及一种制备光学活性(R)-2-苯氧基丙酸衍生物的方法。更具体地说，本发明涉及一种利用对取代苯酚衍生物和烷基(S)-2-芳基磺酰氧基丙酸酯作为起始原料，在碱金属盐作为碱和烃溶剂存在下，在60至100°C下反应制备高纯度的光学活性(R)-2-苯氧基丙酸衍生物的方法。
• Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents
  作者：Daisuke Hirose、Martin Gazvoda、Janez Košmrlj、Tsuyoshi Taniguchi

  DOI：10.1021/acs.joc.8b00486

  日期：2018.4.20

  2-Arylazocarboxylate and 2-arylazocarboxamide derivatives can serve as replacements of typical Mitsunobu reagents such as diethyl azodicarboxylate. A systematic investigation of the reactivity and physical properties of those azo compounds has revealed that they have an excellent ability as Mitsunobu reagents. These reagents show similar or superior reactivity as compared to the known azo reagents

  2-芳基偶氮羧酸酯和2-芳基偶氮羧酰胺衍生物可以替代典型的Mitsunobu试剂，例如偶氮二羧酸二乙酯。对这些偶氮化合物的反应性和物理性质的系统研究表明，它们具有出色的Mitsunobu试剂能力。与已知的偶氮试剂相比，这些试剂显示出相似或更高的反应性，并且适用于广泛的底物范围。p ķ一已经研究了底物的空间效应和空间效应，并且可以通过从2-芳基偶氮羧酸酯和2-芳基偶氮甲酰胺衍生物的文库中选择合适的试剂来克服Mitsunobu反应的局限性。例如，通过一锅铁催化的好氧氧化可方便地回收偶氮试剂。代表性的2-芳基偶氮羧酸酯和2-芳基偶氮羧酰胺衍生物的SC-DSC分析显示出高的热稳定性，表明与典型的偶氮试剂相比，这些偶氮试剂具有较低的化学危害。
• Synthesis, conformation analysis and catalytic properties of chiral zirconium complexes containing etherfunctionalized Cp ligands
  作者：Adolphus A.H van der Zeijden、Chris Mattheis

  DOI：10.1016/s0022-328x(99)00164-3

  日期：1999.7

  A novel series of chiral ligands was synthesized having a cyclopentadienyl (Cp) ring attached to an ether moiety. Four chiral monoCp zirconium derivatives contain these ligands in a bidentate Cp/O coordination mode. Complexes 4d, 6d, and 7d bear an aryl group at the end of the ether chain. The racemic complexes 3d and 4d show moderate activity for the polymerisation of ethylene. Complexes 6d and 7d are enantiopure and were used as asymmetric Lewis acid catalysts for the hydrocyanation of benzaldehyde. The negligible enantiomeric excess thereby is due to decomplexation of the weakly coordinated aryl ether side-chains during catalysis. (C) 1999 Elsevier Science S.A. All rights reserved.