2-fluoro-2-(naphthalen-2-yloxy)acetic acid | 74590-72-0

• 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: 2-fluoro-2-(naphthalen-2-yloxy)acetic acid
• 英文别名: 2-Fluoro-2-naphthalen-2-yloxyacetic acid
• CAS: 74590-72-0
• 化学式: C₁₂H₉FO₃
• 分子量: 220.2
• InChiKey: WNQCNJNODQSTSH-UHFFFAOYSA-N

物化性质

• 熔点：
  >100 °C (decomp)
• 沸点：
  385.2±22.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 2-fluoro-2-(naphthalen-2-yloxy)acetic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以86%的产率得到2-fluoro-N-(mesitylsulfonyl)-2-(naphthalen-2-yloxy)acetamide
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators

  摘要：

  Exchange proteins directly activated by cAMP (EPAC) play a central role in various biological functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, we report the synthesis and biochemical evaluation of a series of noncyclic nucleotide EPAC1 activators. Several potent EPAC1 binders were identified including 25g, 25q, 25n, 25u, 25e, and 25f, which promote EPAC1 guanine nucleotide exchange factor activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity toward EPAC over protein kinase A and G protein-coupled receptors. Moreover, 25e, 25f, 25n, and 25u exhibited improved selectivity toward activation of EPAC1 over EPAC2 in cells. Of these, 25u was found to robustly inhibit IL-6-activated signal transducer and activator of transcription 3 (STAT3) and subsequent induction of the pro-inflammatory vascular cell adhesion molecule 1 (VCAM1) cell-adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacological tools for elucidation of EPAC function and promising drug leads for the treatment of relevant human diseases.

  DOI：

  10.1021/acs.jmedchem.9b02094
• 作为产物：
  描述：

  2-萘氧乙酸 在 三氟甲基次氟酸酯 、 水 、 lithium diisopropyl amide 作用下， 生成 2-fluoro-2-(naphthalen-2-yloxy)acetic acid
  参考文献：
  名称：

  .alpha.-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite

  摘要：

  DOI：

  10.1021/ja00534a053

文献信息

• Synthesis of .alpha.-fluorocarbonyl compounds
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04215044A1

  公开（公告）日：1980-07-29

  Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms; each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms; R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms; R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.C group is carbocyclic, heterocyclic or haloheterocyclic, and recovering from the reaction mixture the compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3.

  制备具有化学式R.sup.2 R.sup.2 CFC(O)R.sup.3的有机化合物的过程包括在一个惰性溶剂中的反应混合物中，将ROF和##STR1##在温度为-40°C至-100°C下接触和反应；其中R是1-6个碳原子的多氟聚卤烷基或FOCF.sub.2；R.sup.1是1-6个碳原子的烃基；每个R.sup.2从H，1-17个碳原子的烷基，3-6个碳原子的环烷基，芳香族，杂环芳基中选择，以及这些烷基、环烷基、芳基和杂环芳基被卤素或1-6个碳原子的烷氧基取代；R.sup.3从H，1-16个碳原子的烷基和卤代烷基，3-10个碳原子的环烷基，芳香族和卤代芳香族，OSi(R.sup.1).sub.3，OH，NH.sub.2，1-6个碳原子的烷氧基，芳氧基，NHR.sup.1和NR.sup.1.sub.2中选择，其中R.sup.1是1-6个碳原子的烷基，N-芳基氨基和4-5个碳原子的氮或硫杂环；R.sup.3和一个R.sup.2共同形成一个与C.dbd.C基团为碳环、杂环或卤杂环的二自由基，从反应混合物中回收具有化学式R.sup.2 R.sup.2 CFC(O)R.sup.3的化合物。
• [EN] SELECTIVE NON-CYCLIC NUCLEOTIDE ACTIVATORS FOR THE CAMP SENSOR EPAC1<br/>[FR] ACTIVATEURS NUCLÉOTIDIQUES NON CYCLIQUES SÉLECTIFS POUR LE CAPTEUR DE CAMP EPAC 1
  申请人：UNIV TEXAS

  公开号：WO2021188728A9

  公开（公告）日：2022-08-11
• MIDDLETON W. J.; BINGHAM E. M., J. AMER. CHEM. SOC., 1980, 102, NO 14, 4845-4846
  作者：MIDDLETON W. J.、 BINGHAM E. M.

  DOI：——

  日期：——
• US4215044A
  申请人：——

  公开号：US4215044A

  公开（公告）日：1980-07-29
• .alpha.-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite
  作者：W. J. Middleton、E. M. Bingham

  DOI：10.1021/ja00534a053

  日期：1980.7