| 433244-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 433244-74-7
• 化学式: C₁₁H₉F₃O₃
• 分子量: 246.186
• InChiKey: YBNNPZXUQRORMU-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  338.0±42.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 乙硫醇钠 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Isomeric acetoxy analogs of celecoxib and their evaluation as cyclooxygenase inhibitors

  摘要：

  A group of celecoxib analogs having a SO2NH2 (9a-f), or SO2Me (12a-f), COX-2 pharmacophore at the para-position of the N-1 phenyl ring in conjunction with a C-5 phenyl ring having a variety of substituents (4-, 3-, 2-OAc; 4-Me, 2-OAc, 4-Me, 3-OAc, 4-F,2-OAc) was synthesized for evaluation as cyclooxygenase (COX) inhibitors of the COX-1/COX-2 isozymes. Within this group of compounds, 1-(4-aminosulfonylphenyl)-3-trifluoromethyl-5-(2-acetoxy-4-fluorophenyl)pyrazole (9f) emerged as the most potent (COX-1 IC50 = 0.7 mu M; COX-2 IC50 = 0.015 mu M) and selective (COX-2 selectivity index = 47) inhibitor agent that exhibited good anti-inflammatory activity (ED50 = 42.3 mg/kg) which was lower than the reference drug celecoxib (ED50 = 10.8 mg/kg), but greater than ibuprofen (ED50 = 67.4 mg/kg) and aspirin (ED50 = 128.7 mg/kg). Molecular modeling studies for 9f showed that the SO2NH2 group assumes a position within the secondary pocket of the COX-2 active site wherein the SO2NH2 oxygen atom is hydrogen bonded to the H90 residue (2.90 angstrom), the SO2NH2 nitrogen atom forms a hydrogen bond with L352 (N center dot center dot center dot O = 2.80 angstrom ), and the acetyl group is positioned in the vicinity of the S530 residue where the acetyl oxygen atom undergoes hydrogen bonding to L531 (2.99 angstrom). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.053
• 作为产物：
  描述：

  三氟乙酸乙酯 、 3-甲氧基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  单氟烷基砌块的合成与应用：α-卤代-α-氟酮

  摘要：

  使用 Wu-Colby's 报道了一种高效便捷的单氟烷基试剂 α-卤代-α-氟酮合成方法，包括 α-碘代-α-氟代酮、α-溴代-α-氟代酮和 α-氯代-α-氟代酮。涉及释放三氟乙酸盐的协议。

  DOI：

  10.1002/ejoc.202200137

文献信息

• Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones
  作者：Li-Hua Wang、Jing Zhao

  DOI：10.1002/ejoc.201800680

  日期：2018.8.23

  A detrifluoroacetylation of trifluoromethyl‐β‐diketones has been developed, which allows for the synthesis of succinimides and 1,4‐diketones through cascade Michael addition/retro‐Claisen reaction and nucleophilic substitution/retro‐Claisen reaction.

  已开发出三氟甲基-β-二酮的三氟乙酰化，可通过级联迈克尔加成反应/复古克莱森反应和亲核取代/复古克莱森反应合成琥珀酰亚胺和1,4-二酮。
• Enantioselective Copper-Catalyzed Intermolecular Cyanobenzoyldifluoromethylation of Alkenes: Access to Chiral β-Difluoroacyl Nitriles
  作者：Mougui Fang、Pingjie Wu、Xia Wang、Ziyue Xie、Yali Hou、Yao Liu、Jingjing Wu、Fanhong Wu

  DOI：10.1021/acs.joc.1c02908

  日期：2022.3.18

  thylation of alkenes with iododifluoromethyl ketones and TMSCN has been reported, which provides a particularly valuable route to access chiral β-difluoroacyl nitriles with excellent enantioselectivities. The method permits the efficient cyanation of varied β-difluoroacyl-benzylic radicals in mild conditions with high functional group tolerance. The reaction proceeds through a radical pathway. In order

  已经报道了一种新颖的不对称铜催化烯烃与碘二氟甲基酮和 TMSCN 的分子间氰基苯甲酰基二氟甲基化反应，这为获得具有优异对映选择性的手性 β-二氟酰基腈提供了特别有价值的途径。该方法允许在具有高官能团耐受性的温和条件下有效地氰化各种β-二氟酰基-苄基自由基。该反应通过自由基途径进行。为了深入了解立体化学结果，进行了计算机制研究。