ethyl 2-hydroxy-2-(3-methoxyphenyl)acetate | 220532-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-hydroxy-2-(3-methoxyphenyl)acetate
• 英文别名: 3-methoxy-mandelic acid-ethyl ester；3-Methoxy-mandelsaeure-aethylester；3-Methoxy-phenylglykolsaeure-ethylester
• CAS: 220532-05-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: FLJPWVWIWOYFPD-UHFFFAOYSA-N

物化性质

• 沸点：
  326.6±32.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基苯基乙酸乙酯 在 对甲苯磺酰叠氮 、 C₁₈BF₁₅*(x)H₂O 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 ethyl 2-hydroxy-2-(3-methoxyphenyl)acetate
  参考文献：
  名称：

  硼催化水中α-芳基α-重氮酸酯的OH键插入

  摘要：

  在存在B（C 6 F 5）3 · n H 2 O（2摩尔％）的条件下，开发了水中无催化的α-重氮酸酯插入金属的O–H键，从而获得了一系列的α-羟基酯。好到极好的产量。该反应具有易于操作和广泛的底物范围的特​​点，重要的是，与常规方法相比，不需要金属。重要的是，这种方法进一步扩展了B（C 6 F 5）3在耐水条件下的应用。

  DOI：

  10.1021/acs.orglett.8b01988

文献信息

• Expeditious and novel synthesis of α-hydroxyesters via rhodium–NHC catalyzed arylation of ethyl glyoxalate
  作者：Carolina S. Marques、Anthony J. Burke

  DOI：10.1016/j.tet.2012.05.129

  日期：2012.9

  The rhodium–NHC catalyzed arylation reaction of ethyl glyoxalate with aryl and alkyl boronic acids provides an efficient method for the synthesis of α-hydroxyesters. A wide range of α-hydroxyesters (up to 12) were prepared in good to excellent yields. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. As far as we are aware, this is the first report of this catalytic arylation

  乙二醛草酸乙酯与芳基和烷基硼酸的铑-NHC催化的芳基化反应为合成α-羟基酯提供了一种有效的方法。制备了多种α-羟基酯（最多12种），收率良好至极佳。KO吨卜是选择的基础上，沿与叔戊醇作为溶剂。据我们所知，这是使用这种特定底物类型的铑-NHC催化剂进行的这种催化芳基化的首次报道。
• Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(i)–phosphane and phosphane–phosphite catalysts
  作者：Carolina Silva Marques、Mehmet Dindaroğlu、Hans-Günther Schmalz、Anthony J. Burke

  DOI：10.1039/c3ra47000h

  日期：——

  Herein we report the first application of Rh(I)–phosphane and phosphane–phosphite catalysts in the enantioselective catalytic arylation of ethyl glyoxylate with organoboron reagents, providing access to ethyl mandelate derivatives in high yield (up to 99%) and moderate to very good enantioselectivities (up to 75% ee). Commercial phosphane ligands, such as (R)-MonoPhos and (R)-Phanephos were tested

  本文中，我们报道了Rh（I）-膦和亚膦酸亚膦酯催化剂在乙醛酸乙酯与有机硼试剂的对映选择性催化芳基化中的首次应用，从而提供了高收率（高达99％）且中等至非常好地获得扁桃酸乙酯衍生物的途径。对映选择性（高达75％ee）。测试了商业膦配体，例如（R）-MonoPhos和（R）-Phanephos，以及非商业（R，R）-TADDOL衍生的膦-亚磷酸酯配体。发现那些在手性亚磷酸酯部分的邻位和对位含有大的取代基的配体是最具选择性的。
• Hydroacylation of Activated Ketones Catalyzed by <i>N</i>-Heterocyclic Carbenes
  作者：Audrey Chan、Karl A. Scheidt

  DOI：10.1021/ja060833a

  日期：2006.4.1

  N-heterocyclic carbenes derived from triazolium salts are effective catalysts between 10 and 15 mol % for the hydroacylation of activated ketones. The reducing equivalent is generated via the interaction of a nucleophilic carbene species and an aromatic aldehyde. The subsequent alcohol product can undergo an acylation event with the resulting acyl heteroazolium intermediate formed in situ between the NHC and the aldehyde. This unprecedented multiple bond-forming reaction can accommodate aromatic aldehydes as the hydride source and various electron-deficient ketones. Preliminary mechanistic evidence indicates that the reduction and acylation steps are sequential operations. The intramolecular variant of this organocatalytic reaction affords benzofuranones in good yield.
• Levy; Pernot, Bulletin de la Societe Chimique de France, 1931, vol. <4> 49, p. 1730,1733
  作者：Levy、Pernot

  DOI：——

  日期：——
• Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)–NHC catalysts and organoboron reagents
  作者：Carolina S. Marques、Anthony J. Burke

  DOI：10.1016/j.tetasy.2013.04.011

  日期：2013.6

  Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. (KOBu)-Bu-t was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts. (C) 2013 Elsevier Ltd. All rights reserved.