2-羟基-2-(4-甲氧基苯基)丙酸甲酯 | 101970-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-羟基-2-(4-甲氧基苯基)丙酸甲酯
• 英文名称: 2-hydroxy-2-(4-methoxyphenyl)propionic acid methyl ester
• 英文别名: (+/-)-methyl 2-hydroxy-2-(4-methoxyphenyl)propionate；methyl 2-hydroxy-2-(4-methoxyphenyl)propanoate；methyl 2-(4-methoxyphenyl)lactate
• CAS: 101970-29-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: KPYPECQJTDNGTE-UHFFFAOYSA-N

物化性质

• 沸点：
  135 °C(Press: 0.1 Torr)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 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

• 作为反应物：
  描述：

  2-羟基-2-(4-甲氧基苯基)丙酸甲酯 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium hydride 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 11.5h， 生成 3-(4-methoxyphenyl)-5-[(4-methylphenyl)sulfonyl]-1-propyl-1,2,3,4-tetrahydropyridin-2-one
  参考文献：
  名称：

  New synthesis of 3-aryl-N-n-propyl-piperidines

  摘要：

  The synthesis of 3 -aryl-N-n-propyl-piperidines is described in six steps starting from a-sulfonyl acetamide via the formal [3+3] cycloaddition reaction of the latter into glutarimide. The pathway involves an efficient cycloaddition and regioselective reduction, and yields useful building blocks for heterocyclic chemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00282-x
• 作为产物：
  描述：

  2-(4-Methoxy-phenyl)-2-trimethylsilanyloxy-propionic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-羟基-2-(4-甲氧基苯基)丙酸甲酯
  参考文献：
  名称：

  酰基咪唑对芳香族酮的电还原酰化

  摘要：

  在氯代三甲基硅烷的存在下，通过电还原作用实现芳族酮与酰基咪唑的分子间还原偶联，得到α-三甲基甲硅烷氧基酮和酯。使用Bu 4 NPF 6作为支持电解质和THF中的Pb阴极可获得最佳结果。通过在THF中用TBAF处理，将含α-三甲基甲硅烷氧基的产物转化为相应的α-羟基酮和酯。该方法对于δ-和ε-酮基酰基咪唑的分子内还原偶联也是有效的。

  DOI：

  10.1021/jo051498w

文献信息

• Highly Regioselective Friedel–Crafts Reactions of Electron-Rich Aromatic Compounds with Pyruvate Catalyzed by Lewis Acid-Base: Efficient Synthesis of Pesticide Cycloprothrin
  作者：Yu-Gui Si、Jun Chen、Fan Li、Jin-Hua Li、Ye-Jun Qin、Biao Jiang

  DOI：10.1002/adsc.200505450

  日期：2006.5

  An efficient synthesis of aromatic lactate esters is reported via highly regioselective Friedel–Crafts reactions of electron-rich aromatic compounds with pyruvate ester promoted by TiCl4 in the presence of basic Al2O3. The utility of the reaction is shown by the efficient synthesis of the pesticide cycloprothrin in high yield.

  芳族乳酸酯的有效的合成报道通过用丙酮酸酯通过的TiCl促进富电子的芳族化合物的高度选择性Friedel-Crafts反应4在基本Al的存在2 Ó 3。该反应的实用性以高产率高效合成了农药环丙菊酯显示出来。
• Conformational Analysis of MαNP Esters, Powerful Chiral Resolution and1H NMR Anisotropy Tools – Aromatic Geometry and Solvent Effects on Δδ Values
  作者：Yusuke Kasai、Akinori Sugio、Satoshi Sekiguchi、Shunsuke Kuwahara、Takatoshi Matsumoto、Masataka Watanabe、Akio Ichikawa、Nobuyuki Harada

  DOI：10.1002/ejoc.200600856

  日期：2007.4

  group, the ester carbonyl oxygen, and the methoxy oxygen supports a triangular intramolecular force to stabilize the syn-syn conformation; ii) triangular hydrogen bonding among a hydrogen atom of protic solvents, the ester carbonyl oxygen, and the methoxy oxygen also supports the syn-syn conformation. This hydrogen bonding, as the solvation effect implies, suggests that a similar hydrogen bonding between

  MαNP 酸法非常适用于通过拆分制备对映纯醇，并通过 1H NMR 各向异性效应同时测定其绝对构型，其中 Syn-syn 构象被视为 MαNP 酯的首选构象。然而，MαNP酯的syn-syn构象看起来不稳定，因为两个带负电的氧原子（CH3O和C=O）彼此靠近。为了解决为什么 MαNP 酯采取这种顺-顺构象的问题，研究了芳香族几何结构和溶剂对 1H NMR 各向异性数据的影响，得出以下结论：i) H 之间的类氢键相互作用萘基的-8'、酯羰基氧和甲氧基氧支持三角形分子内力以稳定syn-syn构象；ii) 质子溶剂的氢原子、酯羰基氧和甲氧基氧之间的三角形氢键也支持顺-顺构象。这种氢键，正如溶剂化效应所暗示的，表明 MαNP 酯和硅胶表面的羟基之间的类似氢键将对在硅胶上的 HPLC 中观察到的非对映异构 MαNP 酯的出色区分做出主要贡献。 (© Wiley-VCH Verlag GmbH & Co
• PROCESS FOR PRODUCING 1,2-ETHANEDIOL DERIVATIVES
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0816316A1

  公开（公告）日：1998-01-07

  A process for preparing a 1,2-ethanediol derivative in a high yield by reducing an α-hydroxy carboxylic acid ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium boron hydride compound. A process for preparing a 1,2-ethanediol derivative in a high yield by esterifying an α-hydroxy carboxylic acid derivative to synthesize an α-hydroxy carboxylic acid ester derivative, and reducing this ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium borohydride compound in the same reaction vessel.

  一种在氢化硼钠化合物存在下，通过在原生溶剂或含水非丙烯极性溶剂中还原 α-羟基羧酸酯衍生物，以高产率制备 1，2-乙二醇衍生物的工艺。一种通过酯化α-羟基羧酸衍生物合成α-羟基羧酸酯衍生物，并在同一反应容器中，在有硼氢化钠化合物存在的情况下，在质子溶剂或含水非丙烷极性溶剂中还原该酯衍生物，从而高产率制备1，2-乙二醇衍生物的工艺。
• Al-Catalyzed Enantioselective Alkylation of α-Ketoesters by Dialkylzinc Reagents. Enhancement of Enantioselectivity and Reactivity by an Achiral Lewis Base Additive
  作者：Laura C. Wieland、Hongbo Deng、Marc L. Snapper、Amir H. Hoveyda

  DOI：10.1021/ja053259w

  日期：2005.11.1

  An Al-catalyzed enantioselective method for additions of Me2Zn and Et2Zn to alpha-ketoesters bearing aromatic, alkenyl, and alkyl substituents is disclosed. Transformations are promoted in the presence of a readily available amino acid-based ligand and afford the desired products in excellent yields and in up to 95% ee. Investigations described illustrate that the presence of a Lewis basic additive can lead to significant enhancements in efficiency and enantioselectivity. A mechanistic model that provides a rationale for such effects is provided.
• Electrocatalytic carboxylation of aromatic ketones with carbon dioxide in ionic liquid 1-butyl-3-methylimidazoliumtetrafluoborate to α-hydroxy-carboxylic acid methyl ester
  作者：Qiuju Feng、Kelong Huang、Suqin Liu、Jingang Yu、Fangfei Liu

  DOI：10.1016/j.electacta.2011.03.061

  日期：2011.5

  A new electrochemical procedure for the electrocatalytic carboxylation of aromatic ketones with carbon dioxide in ionic liquid, 1-butyl-3-methylimidazolium tetrafluoborate(BMIMBF4), to alpha-hydroxycarboxylic acid methyl ester was investigated for the first time. The electrochemical behavior of acetophenone in BMIMBF4 was studied by cyclic voltammetry with a reduction peak at -1.9V (vs. Ag). The electrolyses experiments were carried out in an undivided cell under mild conditions without any toxic solvents, catalysts and supporting electrolytes, followed by addition of an alkylating agent, affording the alpha-hydroxycarboxylic acid methyl ester in a moderate yield (62%). The results showed that the yields were strongly affected by various factors: temperature, current density, charge passed, electrode material and substrate concentration. Moreover, the ionic liquid was successfully recycled for this reaction. (C) 2011 Elsevier Ltd. All rights reserved.