(r)-3-(4-氟苯基)-2-羟基丙酸甲酯 | 124980-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (r)-3-(4-氟苯基)-2-羟基丙酸甲酯
• 中文别名: (R)-3-(4-氟苯基)-2-羟基丙酸甲酯
• 英文名称: (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate
• 英文别名: (2R)-3-(4'-Fluorophenyl)-2-hydroxypropionic Acid Methyl Ester；(R)-3-(4-fluorophenyl)-2-hydroxypropionic acid methyl ester；Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate；methyl (2R)-3-(4-fluorophenyl)-2-hydroxypropanoate
• CAS: 124980-98-9
• 化学式: C₁₀H₁₁FO₃
• 分子量: 198.194
• InChiKey: OKWFDTMQPLAWLR-SECBINFHSA-N

物化性质

• 沸点：
  291.7±25.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (r)-3-(4-氟苯基)-2-羟基丙酸甲酯 在 palladium on activated charcoal 2,6-二甲基吡啶 、 lithium hydroxide 、 氢气 、 sodium hydride 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.17h， 生成 (alphaR)-alpha-[(3S)-3-(叔-丁基氧羰基氨基)-4-甲基-2-氧代戊基]-4-氟-苯丙酸2-丙烯-1-基酯
  参考文献：
  名称：

  Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters

  摘要：

  The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide alpha,beta-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 mu M), the ketomethylene isosteres and tripeptide alpha,beta-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 mu M). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 mu M is obtained by condensation of the Phe-Phe dipeptide alpha,beta-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.065
• 作为产物：
  描述：

  对氟苯甲醛 在 盐酸 、 乙二胺四乙酸 、 formate dehydrogenase (cytochrome) 、 D-lactate dehydrogenase from Staphylococcus epidermidis 、 β-烟酰胺腺嘌呤二核苷酸 、 甲酸铵 、 2-巯基乙醇 作用下， 以 水 为溶剂， 反应 10.0h， 生成 (r)-3-(4-氟苯基)-2-羟基丙酸甲酯
  参考文献：
  名称：

  Development of a Continuous Enzymatic Process for the Preparation of (R)-3-(4-Fluorophenyl)-2-hydroxy Propionic Acid

  摘要：

  While many methods have been reported for the synthesis of chiral 2-hydroxy acids, few of them have proven to be reliable toward the synthesis of the title compound in terms of overall yield and enantioselectivity. Herein we describe a continuous enzymatic process for an efficient synthesis of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid at multikilogram scale with a high space-time yield (560 g/(L.d)) using a membrane reactor. The product was generated in excellent enantiomeric excess (ee > 99.9%) and good overall yield (68-72%).

  DOI：

  10.1021/op010232y

文献信息

• Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
  申请人：——

  公开号：US20010047006A1

  公开（公告）日：2001-11-29

  Compounds of the formula: 1 where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the picornaviral 3C protease. Also disclosed are compounds of the formula: 2 where the formula variables are as defined herein that advantageously inhibit or block the biological activity of the picornaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picornaviruses, such as rhinovirus 3C proteases. Intermediates and synthetic methods for preparing such compounds are also described.

  披露了具有以下公式的化合物： 1 其中公式变量如本文所述定义，这些化合物能够有优势地抑制或阻断小RNA病毒3C蛋白酶的生物学活性。还披露了具有以下公式的化合物： 2 其中公式变量如本文所述定义，这些化合物能够有优势地抑制或阻断小RNA病毒3C蛋白酶的生物学活性。这些化合物以及含有这些化合物的药物组合物对于治疗感染了一种或多种小RNA病毒的患者或宿主是有用的，例如鼻病毒3C蛋白酶。还描述了用于制备这些化合物的中间体和合成方法。
• Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides
  作者：Mark D. Levin、John M. Ovian、Jacquelyne A. Read、Matthew S. Sigman、Eric N. Jacobsen

  DOI：10.1021/jacs.0c07043

  日期：2020.9.2

  facilitated the development of an improved catalyst providing higher enantioselectivity with lower catalyst loadings. The versatility of the difluoroalkyl bromide products was demonstrated via highly enantiospecific substitution reactions with suitably reactive nucleophiles. The origins of enantioselectivity were investigated using computed interaction energies of simpli-fied catalyst and substrate structures

  我们报告了碘芳烃催化的 β,β-二氟烷基卤化物结构单元的对映选择性合成。该转化涉及 α-溴苯乙烯的氧化重排，使用 HF-吡啶作为氟化物源，m-CPBA 作为化学计量氧化剂。确定了催化剂分解途径，该途径与催化剂结构-活性关系研究相结合，促进了改进催化剂的开发，该催化剂以较低的催化剂负载量提供更高的对映选择性。二氟烷基溴产品的多功能性通过与适当反应性亲核试剂的高度对映特异性取代反应得到证明。使用简化的催化剂和底物结构的计算相互作用能研究对映选择性的起源，
• Organocatalytic synthesis of optically active aryllactic acid derivatives from<i>β</i>-ketosulfoxides
  作者：Francesca Capitta、Nicola Melis、Francesco Secci、Giuseppe Romanazzi、Angelo Frongia

  DOI：10.1080/17415993.2014.946506

  日期：2014.11.2

  The organocatalytic synthesis of new α-acyloxy-3-arylpropionic thioesters has been accomplished providing some enantioenriched important aryllactic acid derivatives in good yield and enantioselectivities. GRAPHICAL ABSTRACT

  新的α-酰氧基-3-芳基丙酸硫酯的有机催化合成已经完成，以良好的收率和对映选择性提供了一些对映体富集的重要芳基乳酸衍生物。图形概要
• [EN] ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES, AND MATERIALS FOR THEIR SYNTHESIS<br/>[FR] COMPOSES ET COMPOSITIONS ANTI-PICORNAVIRUS; UTILISATIONS PHARMACEUTIQUES ET MATERIAUX EMPLOYES POUR LEUR SYNTHESE
  申请人：AGOURON PHARMA

  公开号：WO2001040189A1

  公开（公告）日：2001-06-07

  Compounds of formula (I), where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the picornaviral 3C protease. Also disclosed are compounds of formula (II) where the formula variables are as defined herein that advantageously inhibit or block the biological activity of the picornaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picornaviruses, such as rhinovirus 3C proteases. Intermediates and synthetic methods for preparing such compounds are also described.

  本发明披露了式(I)的化合物，其中式变量如本文所定义，这些化合物有利地抑制或阻断了小肠病毒3C蛋白酶的生物活性。本发明还披露了式(II)的化合物，其中式变量如本文所定义，这些化合物有利地抑制或阻断了小肠病毒3C蛋白酶的生物活性。这些化合物以及含有这些化合物的药物组合物，对于治疗感染一种或多种小肠病毒（如鼻病毒3C蛋白酶）的患者或宿主非常有用。还描述了制备这些化合物的中间体和合成方法。
• Novel Piperidine Derivatives
  申请人：Austin Talbir

  公开号：US20080207688A1

  公开（公告）日：2008-08-28

  The present invention provides a compound of a formula (I): wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a chemokine (such as CCR3) mediated disease state.

  本发明提供了一个式(I)的化合物，其中变量在此定义；以及制备此类化合物的过程；以及将此类化合物用于治疗趋化因子（如CCR3）介导的疾病状态。