5-氟吡啶-2,3-二甲酸二甲酯 | 155702-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-氟吡啶-2,3-二甲酸二甲酯
• 英文名称: dimethyl 5-fluoro-2,3-pyridinedicarboxylate
• 英文别名: Dimethyl 5-fluoropyridine-2,3-dicarboxylate
• CAS: 155702-14-0
• 化学式: C₉H₈FNO₄
• 分子量: 213.165
• InChiKey: UYCFMOIVNGROIO-UHFFFAOYSA-N

物化性质

• 沸点：
  261.3±40.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(4-氟苯基)甲基]-2,5-吡咯烷二酮 、 5-氟吡啶-2,3-二甲酸二甲酯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 3-Fluoro-7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel tricyclic HIV-1 integrase inhibitors by modification of its pyridine ring

  摘要：

  This communication details both the syntheses and biological evaluation of a novel class of HIV-1 integrase inbibitors. When the quinoline moiety is replaced with the quinoxoline moiety, the antiviral activity is significantly compromised. Similarly, introduction of imidazole to replace the pyridine ring is deleterious to the potency of the compound against the enzyme. Substitution at the 3-position of the pyridine has been investigated. The presence of the pyridine ring in the tricyclic core is preferred for antiviral activity against HIV integrase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.018
• 作为产物：
  描述：

  dimethyl 1-dimethylamino-5-fluoro-1,4-dihydro-2,3-pyridinedicarboxylate 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以75%的产率得到5-氟吡啶-2,3-二甲酸二甲酯
  参考文献：
  名称：

  使用2-氟-2-烯丙基N，N-二甲基hydr的[4 + 2]-环加成反应：3-氟吡啶及其二氢或四氢衍生物的合成

  摘要：

  由2-氟-2-烯烃制备的N，N-二甲基hydr与丙烯酸甲酯，乙炔二羧酸二甲酯和醌进行平滑的[4 + 2]-环加成反应。所得到的3-氟吡啶或其二氢和四氢衍生物可以公平地分离到良好的收率。

  DOI：

  10.1016/0022-1139(93)02932-5

文献信息

• Phosphonate Analogs Of Hiv Integrase Inhibitor Compounds
  申请人：Cai R. Zhenhong

  公开号：US20080076738A1

  公开（公告）日：2008-03-27

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明公开了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物、其受保护的中间体以及用于抑制HIV整合酶的方法。
• [4+2]-Cycloaddition reactions employing 2-fluoro-2-alkenal N,N-dimethylhydrazones: synthesis of 3-fluoropyridines and dihydro or tetrahydro derivatives thereof
  作者：Somnath Ghosh、Manfred Schlosser

  DOI：10.1016/0022-1139(93)02932-5

  日期：1994.4

  N,N-Dimethylhydrazones prepared from 2-fluoro-2-alkenals undergo smooth [4+2]-cycloaddition reactions with methyl acrylate, dimethyl acetylenedicarboxylates and quinones. The resulting 3-fluoropyridines, or dihydro and tetrahydro derivatives thereof, can be isolated in fair to good yield.

  由2-氟-2-烯烃制备的N，N-二甲基hydr与丙烯酸甲酯，乙炔二羧酸二甲酯和醌进行平滑的[4 + 2]-环加成反应。所得到的3-氟吡啶或其二氢和四氢衍生物可以公平地分离到良好的收率。
• Design, synthesis, and biological evaluation of novel tricyclic HIV-1 integrase inhibitors by modification of its pyridine ring
  作者：Sammy E. Metobo、Haolun Jin、Manuel Tsiang、Choung U. Kim

  DOI：10.1016/j.bmcl.2006.05.018

  日期：2006.8

  This communication details both the syntheses and biological evaluation of a novel class of HIV-1 integrase inbibitors. When the quinoline moiety is replaced with the quinoxoline moiety, the antiviral activity is significantly compromised. Similarly, introduction of imidazole to replace the pyridine ring is deleterious to the potency of the compound against the enzyme. Substitution at the 3-position of the pyridine has been investigated. The presence of the pyridine ring in the tricyclic core is preferred for antiviral activity against HIV integrase. (c) 2006 Elsevier Ltd. All rights reserved.