(3-三氟甲基苯甲酰)乙酸乙酯 | 1717-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3-三氟甲基苯甲酰)乙酸乙酯
• 中文别名: 3-氧代-3-(3-三氟甲基苯基)丙酸乙酯
• 英文名称: ethyl (3-trifluoromethylbenzoyl)acetate
• 英文别名: ethyl 3-oxo-3-(3-(trifluoromethyl)phenyl)propanoate；ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate
• CAS: 1717-42-6
• 化学式: C₁₂H₁₁F₃O₃
• mdl: MFCD03424819
• 分子量: 260.213
• InChiKey: YCHPVUWFIZXXPI-UHFFFAOYSA-N

物化性质

• 沸点：
  250-251 °C (lit.)
• 密度：
  1.267 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2918300090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封于阴凉处避光保存。

反应信息

• 作为反应物：
  描述：

  (3-三氟甲基苯甲酰)乙酸乙酯 在 sodium hydride 、 溶剂黄146 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 32.0h， 生成 1,2-Dihydro-2-(4-chlorophenyl)-4-[3-(trifluoromethyl)phenyl]-6-methyldipyrazolo[3,4-b:3',4'-d]pyridine-3(6H)-one
  参考文献：
  名称：

  Structure–activity studies of a series of dipyrazolo[3,4- b :3′,4′- d ]pyridin-3-ones binding to the immune regulatory protein B7.1

  摘要：

  The interaction of co-stimulatory molecules on T cells with 137 molecules on antigen presenting cells plays an important role in the activation of naive T cells. Consequently, agents that disrupt these interactions should have applications in treatment of transplant rejection as well as autoimmune diseases. To this end, specific small molecule inhibitors of human B7.1 were identified and characterized. Herein, we report the identification of potent small molecule inhibitors of the B7.1-CD28 interaction. In a high-throughput screen we identified several leads that prevented the interaction of B7.1 with CD28 with activities in the nanomolar to low micromolar range. One of these, the dihydrodipyrazolopyridinone 1, was subsequently shown to bind the V-like domain of human B7.1 at equimolar stoichiometry. With this as a starting point, we report here the synthesis and initial in vitro structure-activity relationships of a series of these compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00183-4
• 作为产物：
  描述：

  3-三氟甲基苯甲酸 在 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (3-三氟甲基苯甲酰)乙酸乙酯
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360

文献信息

• Access to β-Keto Esters by Palladium-Catalyzed Carbonylative Coupling of Aryl Halides with Monoester Potassium Malonates
  作者：Signe Korsager、Dennis U. Nielsen、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1002/anie.201304072

  日期：2013.9.9

  New tricks for an old dog: The Pd‐catalyzed carbonylative α‐arylation of monoethyl potassium malonates with aryl bromides and reactive aryl chlorides provides a simple and direct route to aryl β‐ketoesters. Because only stoichiometric amounts of carbon monoxide are employed, the method is ideal for the introduction of carbon isotopes into more complex structures.

  老狗的新招数：丙二酸单乙酯钾的Pd催化羰基α-芳基化与芳基溴化物和反应性芳基氯化物的合成提供了一条简单而直接的途径制备芳基β-酮酸酯。由于仅使用化学计量的一氧化碳，因此该方法非常适合将碳同位素引入更复杂的结构中。
• [EN] PHENETHYLAMIDE DERIVATIVES AND THEIR HETEROCYCLIC ANALOGUES<br/>[FR] DÉRIVÉS DE PHÉNÉTHYLAMIDE ET LEURS ANALOGUES HÉTÉROCYCLIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2010044054A1

  公开（公告）日：2010-04-22

  The invention relates to novel phenethylamide derivatives and their heterocyclic analogues of formula (I), wherein A, B, R1, R2 and R3 are as described in the application, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.

  这项发明涉及新型苯乙酰胺衍生物及其异环类似物，其化学式为(I)，其中A、B、R1、R2和R3如申请中所述，并且涉及将这种化合物或这种化合物的药用可接受盐用作药物，特别是促进睡眠的药物受体拮抗剂。
• A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-<i>b</i>]pyridazin-4(1<i>H</i>)-ones
  作者：Cun Tan、Haoyue Xiang、Qian He、Chunhao Yang

  DOI：10.1002/ejoc.201500422

  日期：2015.6

  A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones from N-aminopyrroles was developed. This tandem reaction involves a Conrad–Limpach-type reaction, including the thermal condensation of N-aminopyrroles with the carbonyl group of β-oxo esters followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad–Limpach quinoline

  开发了一种一锅铜 (II) 催化串联合成 2-取代的吡咯并 [1,2-b] 哒嗪-4(1H)-酮从 N-氨基吡咯。这种串联反应涉及 Conrad-Limpach 型反应，包括 N-氨基吡咯与 β-氧代酯的羰基的热缩合，然后是席夫碱中间体的环化。与传统的 Conrad-Limpach 喹啉合成相比，我们在此首次成功地将铜 (II) 作为催化剂应用于该转化中，以提供 2-取代的吡咯并[1,2-b]哒嗪-4(1H)-酮。大多数带有给电子 (EDG) 和吸电子 (EWG) 基团的基材都适用于该程序。相应的产品可以直接转化为多种吡咯并[1,2-b]哒嗪用于药物发现和材料科学。
• SUBSTITUTED AZOLE AROMATIC HETEROCYCLES AS INHIBITORS OF 11BETA-HSD-1
  申请人：Bartberger D. Michael

  公开号：US20080021022A1

  公开（公告）日：2008-01-24

  Compounds of formula I and IV are described and have therapeutic utility, particularly in the treatment of diabetes, obesity and related conditions and disorder: wherein the variables A-B, R 1 , R 2 , m, and Q are described herein.

  化合物的公式I和IV已经描述，并具有治疗效用，特别是在治疗糖尿病、肥胖和相关疾病和紊乱方面： 其中变量A-B、R1、R2、m和Q在此处描述。
• [EN] PYRAZOLONE DERIVATIVES AS NITROXYL DONORS<br/>[FR] DÉRIVÉS DE PYRAZOLONE UTILISÉS EN TANT QUE DONNEURS DE NITROXYLE
  申请人：CARDIOXYL PHARMACEUTICALS INC

  公开号：WO2015183839A1

  公开（公告）日：2015-12-03

  The disclosed subject matter provides pyrazolone derivative compounds, pharmaceutical compositions comprising such compounds, kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  所披露的主题提供了吡唑酮衍生物化合物，包括这些化合物的药物组合物，包括这些化合物的试剂盒，以及使用这些化合物或药物组合物的方法。具体而言，所披露的主题提供了使用这些化合物或药物组合物治疗心力衰竭的方法。