3-(3-甲氧基苯基)-3-羟基丙酸甲酯 | 72719-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(3-甲氧基苯基)-3-羟基丙酸甲酯
• 英文名称: methyl 3-(3-methoxyphenyl)-3-hydroxypropanoate
• 英文别名: Propanoic acid, 3-hydroxy-3-(3-methoxyphenyl), methyl ester；methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate
• CAS: 72719-08-5
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: FNBHACUOQNHQRF-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±32.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)
• 保留指数：
  1634

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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

• 作为反应物：
  描述：

  3-(3-甲氧基苯基)-3-羟基丙酸甲酯 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到methyl 3-(acetyloxy)-3-(3-methoxyphenyl)propanoate
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-3-氧丙酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到3-(3-甲氧基苯基)-3-羟基丙酸甲酯
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004

文献信息

• Cyclization substrates and 6.alpha.-substituted 19-norsteroid derivatives
  申请人：Akzona Incorporated

  公开号：US04186142A1

  公开（公告）日：1980-01-29

  Novel cyclization substrates of the formula: ##STR1## wherein: (a) R.sub.1 is H or alkyl of one to four carbons; (b) R.sub.2 is H or alkyl of one to four carbons, with the proviso that R.sub.1 is H when R.sub.2 is alkyl; and with the proviso that P.sub.2 is H when R.sub.1 is alkyl; (c) R.sub.3 is a leaving group selected from the group consisting of OH, alkoxy of one to four carbons, alkoxyalkyoxy of from two to about four carbons, acyloxy of from about one to about seven carbons, and trialkylsilyloxy; (d) R.sub.4 is halogen, alkoxy of from one to four carbons, hydrocarbyl of from one to about four carbons, hydrocarbyl of from one to about four carbons substituted by one or more (1) halogens or (2) alkoxy moieties of from one to two carbons; and (e) R.sub.5 is H, alkyl of one to six carbons, hydroxy, or an esterified or estherified moiety of (1) less than eight carbons selected from the group consisting of alkoxy, trialkylsilyloxy, aralkyloxy, cyclo-alkoxy, and heterocyclo-oxy radicals; (2) .alpha.-alkoxyalkoxy of from two to four carbons, and (3) acyloxy of from one to seven carbons; leads by way of a cyclization step to 6.alpha.-substituted steroidal derivatives of the formula: ##STR2## wherein R.sub.4 and R.sub.5 have the meaning above and R.sub.6 is alkyl of from one to about four carbons. The compounds of the formulae VI, VII and VIII are important intermediates for preparing wellknown biologically active 6.alpha.-substituted steroids.

  化合物的新颖环化底物的结构式为： ##STR1## 其中：(a) R.sub.1为H或1-4个碳的烷基；(b) R.sub.2为H或1-4个碳的烷基，但当R.sub.2为烷基时，R.sub.1为H；当R.sub.1为烷基时，P.sub.2为H；(c) R.sub.3为选择自羟基，1-4个碳的烷氧基，2-4个碳的烷氧基烷氧基，约1-7个碳的酰氧基和三烷基硅氧基的离去基；(d) R.sub.4为卤素，1-4个碳的烷氧基，1-4个碳的烃基，1-4个碳的烃基，其中一个或多个被(1)卤素或(2)1-2个碳的烷氧基取代；(e) R.sub.5为H，1-6个碳的烷基，羟基，或酯化或酰化基团，选择自：(1)少于8个碳的烷氧基，三烷基硅氧基，芳基烷氧基，环烷氧基和杂环氧基基团；(2)2-4个碳的.alpha.-烷氧基烷氧基；(3)1-7个碳的酰氧基。通过环化步骤，导致6.alpha.-取代类固醇衍生物的结构式： ##STR2## 其中R.sub.4和R.sub.5具有上述含义，R.sub.6是1-4个碳的烷基。公式VI、VII和VIII的化合物是制备已知的生物活性6.alpha.-取代类固醇的重要中间体。
• Optically active alkyl 3-aryl-3-hydroxypropionates and a method for producing thereof
  申请人：CHISSO CORPORATION

  公开号：EP0451668A2

  公开（公告）日：1991-10-16

  The invention relates to optically active alkyl 3-aryl-3-hydroxypropionates represented by the general formula: wherein R¹, R², R³, R ⁴ and R⁵ are hydrogen, hydroxyl, alkoxy of 1-4 carbon atoms, benzyloxy, flurorine, chlorine or bromine and R⁶ is alkyl, and a method for producing the above compounds.

  本发明涉及由通式表示的光学活性 3-芳基-3-羟基丙酸烷基酯： 其中 R¹、R²、R³、R⁴ 和 R⁵ 是氢、羟基、1-4 个碳原子的烷氧基、苄氧基、氟、氯或溴，R⁶ 是烷基、 以及生产上述化合物的方法。
• Method for synthesizing chiral beta-hydroxy acid ester compound
  申请人：Wenzhou University

  公开号：US10906860B2

  公开（公告）日：2021-02-02

  A method for synthesizing a chiral β-hydroxy acid ester compound is disclosed. The method includes the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials, using a metal and a chiral ligand as a catalyst to make the raw materials be directly and fully reacted in an organic solvent and form a reaction solution, and separating and purifying the reaction solution to obtain the highly stereoselective β-hydroxy acid ester compound. The beneficial effects are mainly embodied in: 1. simple operation; 2. rapidly constructing a highly stereoselective β-hydroxy acid ester skeleton structure molecule; 3. high reaction yield and good stereoselectivity. Therefore, the invention has high basic research significance, industrial production value and social economic benefit.

  本发明公开了一种合成手性β-羟基酸酯化合物的方法。该方法包括以下步骤：以醛类化合物和丙二酸单烷基酯为原料，以金属和手性配体为催化剂，使原料在有机溶剂中直接充分反应，形成反应溶液，分离纯化反应溶液，得到高立体选择性的β-羟基酸酯化合物。其优点主要体现在1.操作简单；2.快速构建高立体选择性的β-羟基酸酯骨架结构分子；3.反应产率高，立体选择性好。因此，本发明具有较高的基础研究意义、工业生产价值和社会经济效益。
• Process for the production of optically active alkyl 3-aryl-3-hydroxypropionates
  申请人：CHISSO CORPORATION

  公开号：EP0451668B1

  公开（公告）日：1997-08-13
• METHOD FOR SYNTHESIZING CHIRAL BETA-HYDROXY ACID ESTER COMPOUND
  申请人：Wenzhou University

  公开号：US20200190013A1

  公开（公告）日：2020-06-18

  A method for synthesizing a chiral β-hydroxy acid ester compound is disclosed. The method includes the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials, using a metal and a chiral ligand as a catalyst to make the raw materials be directly and fully reacted in an organic solvent and form a reaction solution, and separating and purifying the reaction solution to obtain the highly stereoselective β-hydroxy acid ester compound. The beneficial effects are mainly embodied in: 1. simple operation; 2. rapidly constructing a highly stereoselective β-hydroxy acid ester skeleton structure molecule; 3. high reaction yield and good stereoselectivity. Therefore, the invention has high basic research significance, industrial production value and social economic benefit.