Ethyl 3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | 160427-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Ethyl 3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 160427-15-6
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: RMVHMSPOGRIKOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate 在 W-2 Raney nickel 盐酸 、 氢气 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 6-(4-羟基苯基)吡嗪-3(2H)-酮
  参考文献：
  名称：

  Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2H)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2H)-pyridazinones

  摘要：

  描述了一种从3,5-二取代的4,5-二氢异噁唑出发，高效制备6-取代的3(2H)-吡嗪酮和6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮的方法。通过六羰基钼或催化氢化促进异噁唑啉环的N-O键断裂，获得了α-羟基γ-酮酯4a-f，这些酯在室温或回流条件下与水合肼反应生成6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮5a-f或6-取代的3(2H)-吡嗪酮6a-f，且收率较高。该协议的灵活性通过从已知的β-核糖硝基甲烷8合成C-核糖苷7得到了验证。此外，还开发了一种分子内版本的方法来制备已知的抗溃疡三环3(2H)-吡嗪酮12。

  DOI：

  10.1055/s-1994-25663
• 作为产物：
  描述：

  丙烯酸乙酯 、 2-异丙氧基苯胺 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 生成 Ethyl 3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
  参考文献：
  名称：

  Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2H)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2H)-pyridazinones

  摘要：

  描述了一种从3,5-二取代的4,5-二氢异噁唑出发，高效制备6-取代的3(2H)-吡嗪酮和6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮的方法。通过六羰基钼或催化氢化促进异噁唑啉环的N-O键断裂，获得了α-羟基γ-酮酯4a-f，这些酯在室温或回流条件下与水合肼反应生成6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮5a-f或6-取代的3(2H)-吡嗪酮6a-f，且收率较高。该协议的灵活性通过从已知的β-核糖硝基甲烷8合成C-核糖苷7得到了验证。此外，还开发了一种分子内版本的方法来制备已知的抗溃疡三环3(2H)-吡嗪酮12。

  DOI：

  10.1055/s-1994-25663

文献信息

• Generation of Nitrile Oxides under Nanometer Micelles Built in Neutral Aqueous Media: Synthesis of Novel Glycal-Based Chiral Synthons and Optically Pure 2,8-Dioxabicyclo[4.4.0]decene Core
  作者：Nirbhik Chatterjee、Palash Pandit、Samiran Halder、Amarendra Patra、Dilip K. Maiti

  DOI：10.1021/jo801337k

  日期：2008.10.3

  for chemoselective oxidation of aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media is reported. Their in situ intermolecular 1,3-dipolar cycloaddition (1,3-DC) with olefins in nanometer aqueous micelles occurs with improved stereoselectivity and acceleration of reaction rate toward synthesis of new chiral synthons, 3-(2'-C-3',4',6'-tri-O-benzylglycal)-Delta(2)-isoxazolines and others

  报道了一种在中性水性介质中碘代苯将醛肟化学选择性氧化为腈氧化物的高效策略。他们在纳米水性胶束中与烯烃进行原位分子间1,3-偶极环加成反应（1,3-DC），提高了立体选择性，并加快了反应速度，从而合成了新的手性合成子3-（2'-C-3'， 4′，6′-三-O-苄基糖基）-Delta（2）-异恶唑啉等。用这种绿色方法进行光学纯的2,8-二氧杂双环[4.4.0]癸烯骨架的构建，并通过B3LYP密度泛函理论预测了新的手性中心的立体化学。
• Solid-Supported Nitrile Oxides as Stable and Valuable Reactive Intermediates
  作者：Giuseppe Faita、Mariella Mella、Annalisa Mortoni、Alfredo Paio、Paolo Quadrelli、Pierfausto Seneci

  DOI：10.1002/1099-0690(200204)2002:7<1175::aid-ejoc1175>3.3.co;2-q

  日期：2002.4
• COMPOUNDS, COMPOSITIONS, PROCESSES OF MAKING, AND METHODS OF USE RELATED TO INHIBITING MACROPHAGE MIGRATION INHIBITORY FACTOR
  申请人：Sielecki-Dzurdz Thais

  公开号：US20080113997A1

  公开（公告）日：2008-05-15

  The present invention provides a compound having Formula I or II: wherein B, R, X, Ar, and Y are defined herein, pharmaceutically acceptable salts thereof and pharmaceutically acceptable prodrugs thereof. The present invention also provides methods of making and using the compound.
• CHIRAL SYNTHESIS OF ISOXAZOLINES, ISOXAZOLINE COMPOUNDS, AND USES THEREOF
  申请人：Sielecki-Dzurdz Thais

  公开号：US20130172553A1

  公开（公告）日：2013-07-04

  Processes for the chiral syntheses of isoxazolines and intermediates are described. Compounds prepared thereby, and methods of using the compounds are also described.
• USE OF ISOXAZOLINE COMPOUNDS AND COMPOSITIONS IN BLADDER CANCER
  申请人：Taylor, III John Arthur

  公开号：US20130196996A1

  公开（公告）日：2013-08-01

  One embodiment provides a method, comprising treating or preventing at least one disease selected from the group consisting of bladder cancer, weight loss accompanying bladder cancer, bone pain accompanying bladder cancer, bladder cancer carcinoma in-situ (CIS), TA stage bladder cancer, T1 stage bladder cancer, T2 stage bladder cancer, T3 stage bladder cancer, T4 stage bladder cancer, lymph node metastasis therefrom, solid organ metastasis therefrom, bony metastasis therefrom, cachexia/anorexia associated with bladder cancer, generalized wasting syndrome associated with bladder cancer, or a combination thereof, by administering to a subject in need thereof one or more compounds described herein, prodrug thereof, salt thereof, or a combination thereof.