ethyl 2-(2-chlorophenoxy)-3-oxobutanoate | 32565-14-3

• 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-(2-chlorophenoxy)-3-oxobutanoate
• 英文别名: Aethyl-o-chlorphenyl-O-acetylacetat
• CAS: 32565-14-3
• 化学式: C₁₂H₁₃ClO₄
• 分子量: 256.686
• InChiKey: RXTYAHFWZNOJOG-UHFFFAOYSA-N

物化性质

• 沸点：
  145-150 °C(Press: 15 Torr)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-chlorophenoxy)-3-oxobutanoate 在 盐酸肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以3.58 g的产率得到of 4-(2-chlorophenoxy)-3-ethoxy-5-methyl-1H-pyrazole
  参考文献：
  名称：

  Original 2-(3-Alkoxy-1H-pyrazol-1-yl)pyrimidine Derivatives as Inhibitors of Human Dihydroorotate Dehydrogenase (DHODH)

  摘要：

  From a research program aimed at the design of new chemical entities followed by extensive screening on various models of infectious diseases, an original series of 2-(3-alkoxy-1H-pyrazol-1-yl)pyrimidines endowed with notable antiviral properties were found. Using a whole cell measles virus replication assay, we describe here some aspects of the iterative process that, from 2-(4-benzyl-3-ethoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine, led to 2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine and a 4000-fold improvement of antiviral activity with a subnanomolar level of inhibition. Moreover, recent precedents in the literature describing antiviral derivatives acting at the level of the de novo pyrimidine biosynthetic pathway led us to determine that the mode of action of this series is based on the inhibition of the cellular dihydroorotate dehydrogenase (DHODH), the fourth enzyme of this pathway. Biochemical studies with recombinant human DHODH led us to measure IC50 as low as 13 nM for the best example of this original series when using 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone (coenzyme Q(1)) as a surrogate for coenzyme Q(10), the cofactor of this enzyme.

  DOI：

  10.1021/jm501446r
• 作为产物：
  描述：

  重氮基乙酰乙酸乙酯 、 邻氯苯酚 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 ethyl 2-(2-chlorophenoxy)-3-oxobutanoate
  参考文献：
  名称：

  New One-Pot Synthesis of Polysubstituted Benzofurans and Benzo-1,4-dioxines

  摘要：

  It has been revealed that the copper(II) triflate catalyzed reaction of ethyl-2-diazo-3-oxobutanoate with phenols followed by cyclization of the intermediate enol in the presence of polyphosphoric acid is a simple and efficient method of synthesis of polysubstituted benzofurans. The use of pyrocatechol leads to the corresponding substituted 1,4-benzodioxine-2-carboxylates as major products.

  DOI：

  10.1134/s0012500818100051

文献信息

• Pyrazole derivatives as dihydroorotate dehydrogenase (DHODH) inhibitors
  申请人：INSTITUT PASTEUR

  公开号：EP2929883A1

  公开（公告）日：2015-10-14

  The present invention relates to compounds of formula (I) for their use in the treatment and/or prevention of auto-immune or auto-immune related diseases, cancer, viral infections, and central nervous system diseases and disorders, by inhibiting human dehydroorate dehydrogenase (DHODH): Wherein R1, R2, R3, R4 and Ar are as defined in claim 1.

  本发明涉及式（I）化合物，通过抑制人脱氢脱氢酶（DHODH），用于治疗和/或预防自身免疫或自身免疫相关疾病、癌症、病毒感染以及中枢神经系统疾病和失调： 其中 R1、R2、R3、R4 和 Ar 如权利要求 1 所定义。
• WO2015/155680
  申请人：——

  公开号：——

  公开（公告）日：——
• Rathnam; Thatte, Chittaranjan S.; Pise, Abhinay C., Asian Journal of Chemistry, 2010, vol. 22, # 8, p. 6092 - 6098
  作者：Rathnam、Thatte, Chittaranjan S.、Pise, Abhinay C.

  DOI：——

  日期：——
• Sila,B.; Seyda,K., Roczniki Chemii, 1970, vol. 44, p. 2025 - 2028
  作者：Sila,B.、Seyda,K.

  DOI：——

  日期：——