methyl (S)-2-(4-phenoxyphenyl)lactate | 286942-91-4

• 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: methyl (S)-2-(4-phenoxyphenyl)lactate
• 英文别名: methyl (2S)-2-hydroxy-2-(4-phenoxyphenyl)propanoate
• CAS: 286942-91-4
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: UCWOQMAFOBZTPQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  methyl (S)-2-(4-phenoxyphenyl)lactate 在 溶剂黄146 作用下， 生成 (S)-(+)-famoxadone
  参考文献：
  名称：

  Famoxadone: the discovery and optimisation of a new agricultural fungicide

  摘要：

  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.

  DOI：

  10.1002/1526-4998(200102)57:2<143::aid-ps282>3.0.co;2-8
• 作为产物：
  描述：

  2-羟基-2-(4-苯氧基苯基)丙酸 在 咪唑 作用下， 生成 methyl (S)-2-(4-phenoxyphenyl)lactate
  参考文献：
  名称：

  Synthesis and structural analysis of the active enantiomer of famoxadone, a potent inhibitor of cytochrome bc 1

  摘要：

  Famoxadone is a newly commercialized fungicide and potent Q(o)-site inhibitor of cytochrome bet. The S-(-)-enantiomer of famoxadone (the active component) was synthesized by two routes and was analyzed computationally and by X-ray crystallography. The molecule displays an extended conformation with flexibility in the structure imparted by the two terminal phenyl groups. In the crystal lattice, intermolecular hydrogen bonds occur between the NH and the oxygen atoms of the heterocycle. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00164-5