乙基2-(2,4-二氯苯胺基)-2-氧代乙酸酯 | 15313-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙基2-(2,4-二氯苯胺基)-2-氧代乙酸酯
• 英文名称: ethyl 2-(2,4-dichloroanilino)-2-oxo-acetate
• 英文别名: ethyl(2,4-dichlorophenylamino)oxoacetate；(2,4-dichloro-phenyl)-oxalamic acid ethyl ester；Aethylester aus Oxalsaeure-mono-(2.4-dichlor-anilid)；Aethylester aus (2.4-Dichlor-phenyl)-oxamidsaeure；(2,4-Dichlor-phenyl)-oxalamidsaeure-aethylester；N-2',4'-Dichlorphenyl-oxamidsaeure-ethylester；Ethyl 2-(2,4-dichloroanilino)-2-oxoacetate
• CAS: 15313-47-0
• 化学式: C₁₀H₉Cl₂NO₃
• mdl: MFCD00122683
• 分子量: 262.092
• InChiKey: BRUUNEWBCZFVMW-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  乙基2-(2,4-二氯苯胺基)-2-氧代乙酸酯 在 五氯化磷 、 羟胺 、 1-氯苯并三氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 ethyl 5,7-dichloro-4H-1,2,4-benzoxadiazine-3-carboxylate
  参考文献：
  名称：

  Gilchrist, Thomas L.; Harris, C. John; King, Frank D., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2169 - 2174

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯苯胺 、 草酰氯单乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到乙基2-(2,4-二氯苯胺基)-2-氧代乙酸酯
  参考文献：
  名称：

  Design, synthesis and biological evaluation of small molecule inhibitors of CD4-gp120 binding based on virtual screening

  摘要：

  The low-molecular-weight compound JRC-II-191 inhibits infection of HIV-1 by blocking the binding of the HIV-1 envelope glycoprotein gp120 to the CD4 receptor and is therefore an important lead in the development of a potent viral entry inhibitor. Reported here is the use of two orthogonal screening methods, GOLD docking and ROCS shape-based similarity searching, to identify amine-building blocks that, when conjugated to the core scaffold, yield novel analogs that maintain similar affinity for gp120. Use of this computational approach to expand SAR produced analogs of equal inhibitory activity but with diverse capacity to enhance viral infection. The novel analogs provide additional lead scaffolds for the development of HIV-1 entry inhibitors that employ protein-ligand interactions in the vestibule of gp120 Phe 43 cavity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.049

文献信息

• Chattaway; Lewis, Journal of the Chemical Society, 1906, vol. 89, p. 161
  作者：Chattaway、Lewis

  DOI：——

  日期：——
• Petyunin,P.A.; Zakalyuzhnyi,M.V., Journal of general chemistry of the USSR, 1964, vol. 34, p. 26 - 30
  作者：Petyunin,P.A.、Zakalyuzhnyi,M.V.

  DOI：——

  日期：——
• Petyunin,P.A.; Kalugina,Z.G., Journal of general chemistry of the USSR, 1963, vol. 33, # 9, p. 2762 - 2768
  作者：Petyunin,P.A.、Kalugina,Z.G.

  DOI：——

  日期：——
• Triphenylphosphine-Catalyzed Simple Synthesis of Dimethyl 1-Aryl-4-ethoxy-5-oxo-4,5-dihydro-1 H -pyrrole-2,3-dicarboxylates
  作者：Issa Yavari、Mansoureh Aghazadeh、Mohsen Tafazzoli

  DOI：10.1080/10426500211717

  日期：2002.5.1

  Ethyl 2-arylamino-2-oxo-acetates undergo a complex reaction with dimethyl acetylenedicarboxylate in the presence of triphenylphosphine to produce dimethyl 1-aryl-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. Dynamic NMR study of dimethyl 1-(2-methylphenyl)-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole2,3-dicarboxylate shows a fairly high energy barrier (DeltaG(not equal)= 53.2 kJmol(-1)) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.
• GILCHRIST, THOMAS L.;HARRIS, C. JOHN;KING, FRANK D.;PEEK, MICHAEL E.;REES+, J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 8, C. 2169-2173
  作者：GILCHRIST, THOMAS L.、HARRIS, C. JOHN、KING, FRANK D.、PEEK, MICHAEL E.、REES+

  DOI：——

  日期：——