ethyl 2-hydroxy-2-(4-phenoxyphenyl)propionate | 132584-17-9

• 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 2-hydroxy-2-(4-phenoxyphenyl)propionate
• 英文别名: 2-hydroxy-2-(4-phenoxyphenyl)ethyl propionate；ethyl 2-(4-phenoxyphenyl)lactate；ethyl 2-hydroxy-2-(4-phenoxyphenyl)propanoate
• CAS: 132584-17-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: NFJAMPAQUJUQEH-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±30.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)
• LogP：
  2.7 at 20℃
• 表面张力：
  63.6mN/m at 16.5mg/L and 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  ethyl 2-hydroxy-2-(4-phenoxyphenyl)propionate 在 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 3-(2,6-Dimethylanilino)-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione
  参考文献：
  名称：

  Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors

  摘要：

  The cytochrome bc(1) complex (EC 1.10.2.2, bc(1)) is one of the most promising targets for new drugs and agricultural fungicides. Among the existing bc(1) complex inhibitors specifically binding to the Q(o) site, oxazolidinedione derivatives have attracted great attention. With the aim to understand the substituent effects of oxazolidinedione derivatives on the inhibition activity against the bc(1) complex, a series of new oxazolidinedione derivatives were designed, synthesized, and biologically evaluated. The further inhibitory kinetics studies against porcine succinate-cytochrome c reductase (SCR) revealed that the representative compound 8d and famoxadone are both non-competitive inhibitors with respect to the substrate cytochrome c, but competitive inhibitors with respect to substrate decylubiquinol (DBH2). In addition, compound 8d and famoxadone showed, respectively, 35-fold and 15-fold greater inhibitory activity against the porcine SCR than the porcine bc(1) complex, indicating that these two inhibitors not only inhibited the activity of the bc(1) complex, but possibly affect the interaction between the complex II and the bc(1) complex. To our knowledge, this is the first report that famoxadone and its analogs have effects on the interaction between the complex II and the bc(1) complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.008
• 作为产物：
  描述：

  丙酮酸乙酯 、 4-溴联苯醚 在 氮气 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 ethyl 2-hydroxy-2-(4-phenoxyphenyl)propionate
  参考文献：
  名称：

  Fungicidal oxazolidinones

  摘要：

  揭示了利用硫代噁唑烷酮、噁唑烷二酮以及含有它们的农业适用组合物来控制植物病害的方法。

  公开号：

  US05223523A1

文献信息

• Process for preparing fungicidal oxazolidinones and imidazolinones
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP1092712A1

  公开（公告）日：2001-04-18

  The present invention pertains to a process for preparing compounds of Formula I (useful as fungicides and/or intermediates for producing fungicides) wherein Q is O or NH; W is O or S; X is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl or OR4; Y is H or halogen; R1 is C1-C4 alkyl; R4 is C1 -C4 alkyl, C1 -C4 haloalkyl or optionally substituted phenyl; and * represents the location of the chiral center; and important intermediates of Formula II used in that process. The process of this invention comprises treating a compound of Formula II (that is racemic, enantiomerically enriched, or enantiomerically pure at chiral center *), or esters thereof, wherein OR3 is an oxygen-linked coupling agent (and Q, W, X, R1, R4 and * are as previously defined); with phenyl hydrazine in the presence of an acidic catalyst (and preferrably a basic catalyst).

  本发明涉及一种制备Formula I化合物的过程（作为杀菌剂和/或用于生产杀菌剂的中间体），其中Q为O或NH；W为O或S；X为H、卤素、C1-C4烷基、C1-C4卤代烷基或OR4；Y为H或卤素；R1为C1-C4烷基；R4为C1-C4烷基、C1-C4卤代烷基或可选地取代的苯基；*表示手性中心的位置；以及在该过程中使用的Formula II的重要中间体。本发明的过程包括在存在酸性催化剂（最好是碱性催化剂）的情况下，处理Formula II化合物（即在手性中心*处为消旋、对映富集或对映纯的化合物，或其酯），其中OR3为氧键合偶联剂（且Q、W、X、R1、R4和*如前所定义）；与苯基肼发生反应。
• 一种乳酸酯衍生物的合成方法及其产物与应用
  申请人：上海生农生化制品股份有限公司

  公开号：CN106632168A

  公开（公告）日：2017-05-10

  本发明提供了一种乳酸酯衍生物的合成方法，以及该合成方法合成的产物及其应用。所述合成方法的合成路线为：性溶剂中加入化合物IV、化合物III、作为催化剂的碱，然后加入路易斯酸，进行反应，制得所述乳酸酯衍生物I。本发明所提供的乳酸酯衍生物的合成方法，仅通过一步化学反应即制得目标产物，该合成方法的反应条件温和，操作简单，收率较高，成本较低，因此，有利于大规模工业化生产，能够为以拟除虫菊酯类杀虫剂为代表的各种农药或医药产品的后续生产奠定基础，因此，所述合成方法及其产物与应用均具有良好的应用前景与市场潜力。
• Imidazole and triazole carboxylates, and processes for preparing
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05552554A1

  公开（公告）日：1996-09-03

  Processes are described for preparing 2,4-oxazolidinediones having Formula (I) ##STR1## wherein: R.sup.1 is phenyl optionally substituted with 1-2 halogens; or 4-phenoxy, 4-(1-phenethyloxy) or 4-benzyloxy each optionally substituted with R.sup.2 on the phenyl ring; and R.sup.2 is halogen; methyl; or ethyl. 2-Hydroxycarboxylic acid esters are reacted with a carbonylating agent in the presence of a base to give intermediate triazole or imidazole carboxylates. The carboxylates react with phenyl hydrazine in the presence of an acid to give the compounds of Formula (I).

  描述了制备具有式（I）的2,4-噁唑烷二酮的过程，其中：R.sup.1是苯基，可选地取代1-2个卤素; 或4-苯氧基，4-（1-苯乙氧基）或4-苄氧基，每个在苯环上可选地取代R.sup.2; 而R.sup.2是卤素; 甲基; 或乙基。2-羟基羧酸酯在碱的存在下与羰基化试剂反应，形成中间体三唑或咪唑羧酸酯。羧酸酯在酸的存在下与苯基肼反应，形成式（I）的化合物。
• Fungicidal mixtures
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05948805A1

  公开（公告）日：1999-09-07

  Advantageous combinations of an oxazolidinone and cymoxanil (or their agriculturally suitable salts) and their use to control fungus disease in plants are disclosed, the oxazolidinone having the formula ##STR1##

  本发明揭示了一种优势组合物，包括奥沙利啶和茜莫沙胺（或其适用于农业的盐），以及它们在植物中控制真菌病的使用。其中，奥沙利啶的化学式为##STR1##。
• Famoxadone: the discovery and optimisation of a new agricultural fungicide
  作者：Jeffrey A Sternberg、Detlef Geffken、John B Adams、Reiner P�stages、Charlene G Sternberg、Carlton L Campbell、William K Moberg

  DOI：10.1002/1526-4998(200102)57:2<143::aid-ps282>3.0.co;2-8

  日期：2001.2

  Famoxadone (3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione), is a new agricultural fungicide recently commercialized by DuPont under the trade name Famoxate(R) Famoxadone is a member of a new class of oxazolidinone fungicides that demonstrate excellent control of plant pathogens in the Ascomycete, Basidiomycete, and Oomycete classes that infect grapes, cereals, tomatoes, potatoes and other crops. DuPont's entry into the oxazolidinone area resulted from the procurement of 5-methyl-5-phenyl-3-phenylamino-2-thioxo-4-oxazolidinone (1) from Professor Detlef Geffken, then at the University of Bonn, An extensive analog program was initiated immediately after the fungicidal activity of 1 was discovered through routine greenhouse testing. The discovery program in the oxazolidinone area eventually culminated in the advancement of famoxadone to commercial development in the early 1990s. The synthesis of various oxazolidinone ring systems and the development of the structure-activity relationships that led to the discovery of famoxadone are described. (C) 2001 Society of Chemical Industry.