2-(3-三氟甲基苯基)-丙二酸二乙酯 | 1997-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-三氟甲基苯基)-丙二酸二乙酯
• 英文名称: diethyl 2-(3-(trifluoromethyl)phenyl)malonate
• 英文别名: 1,3-diethyl 2-(3-trifluoromethylphenyl)propanedioate；Diethyl 2-[3-(trifluoromethyl)phenyl]propanedioate
• CAS: 1997-28-0
• 化学式: C₁₄H₁₅F₃O₄
• 分子量: 304.266
• InChiKey: XUVNJTKVYGCXEY-UHFFFAOYSA-N

物化性质

• 沸点：
  145-150 °C(Press: 10 Torr)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2917399090

反应信息

• 作为反应物：
  描述：

  2-(3-三氟甲基苯基)-丙二酸二乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二苯醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-bromo-phenoxy)-2-ethyl-7-methoxy-3-(3-trifluoromethyl-phenyl)-quinoline
  参考文献：
  名称：

  Discovery of Novel Quinoline-Based Estrogen Receptor Ligands Using Peptide Interaction Profiling

  摘要：

  Traditional approaches to discovery of selective estrogen receptor modulators (SERMs) have relied on ER binding and cell-based estrogen response element-driven assays to identify compounds that are osteoprotective but nonproliferative in breast and uterine tissues. To discover new classes of potential SERMs, we have employed a cell-free microsphere-based binding assay to rapidly characterize ER alpha interactions with conformation-sensing cofactor or phage display peptides. Peptide profiles of constrained triarenes were compared to known proliferative and nonproliferative ER ligands to discover potent quinoline-based ligands with minimal Ishikawa cell stimulation.

  DOI：

  10.1021/jm040154f
• 作为产物：
  描述：

  3-碘三氟甲苯 、 丙二酸二乙酯 在 copper(l) iodide 、 air 、 biacetyl bis(N-methyl-N-phenylhydrazone) 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到2-(3-三氟甲基苯基)-丙二酸二乙酯
  参考文献：
  名称：

  使用腙配体的铜 (I) 催化 CC 和 CO 偶联反应

  摘要：

  在 90°C 下，芳基碘化物与丙二酸二乙酯在甲苯中的铜催化 CC 偶联反应得到芳基化丙二酸酯，使用 5 mol% 的 CuI 和腙 1a 作为配体，在有氧气氛下以良好的收率。我们还发现甲苯中的 Cul/腙 1b 是一种有效的催化体系，用于芳基溴化物与苯酚的 CO 偶联反应，在 110 °C 有氧气氛下以良好的产率得到芳基醚。

  DOI：

  10.1055/s-0029-1217822

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• Carbon-Selective Difluoromethylation of Soft Carbon Nucleophiles with Difluoromethylated Sulfonium Ylide
  作者：Jiansheng Zhu、Hanliang Zheng、Xiao-Song Xue、Yisa Xiao、Yafei Liu、Qilong Shen

  DOI：10.1002/cjoc.201800383

  日期：2018.11

  highly carbon‐selective difluoromethylation of soft carbon nucleophiles including β‐ketoesters, malonates, oxindoles, benzofuranones and ketene silyl acetals with a difluoromethylated sulfonium ylide under mild conditions was described. Mechanistic studies suggest that these difluoromethylating reactions proceed via a difluorocarbene pathway.

  描述了在温和条件下用二氟甲基化叶立德对软碳亲核试剂（包括β-酮酸酯，丙二酸酯，羟吲哚，苯并呋喃酮和乙烯酮甲硅烷基乙缩醛）进行高碳选择性二氟甲基化。机理研究表明，这些二氟甲基化反应是通过二氟卡宾途径进行的。
• Monofluoromethyl‐Substituted Sulfonium Ylides: Electrophilic Monofluoromethylating Reagents with Broad Substrate Scopes
  作者：Yafei Liu、Long Lu、Qilong Shen

  DOI：10.1002/anie.201704175

  日期：2017.8.7

  Two electrophilic monofluoromethylating reagents, monofluoromethyl(phenyl)sulfonium bis(carbomethoxy)methylide (3 a) and monofluoromethyl(4‐nitrophenyl)sulfonium bis(carbomethoxy)methylide (3 b), and their reactions under mild conditions with a variety of nucleophiles, such as alcohols and malonate derivatives, sulfonic and carboxylic acids, phenols, amides, and N heteroarenes, are described. Mechanistic

  两种亲电单氟甲基化试剂，单氟甲基（苯基）ulf双（羰甲氧基）甲基化物（3a）和单氟甲基（4-硝基苯基）ulf双（羰甲氧基）甲基化物（3b），以及它们在温和条件下与各种亲核试剂的反应作为醇和丙二酸酯的衍生物，描述了磺酸和羧酸，酚，酰胺和N杂芳烃。用氘化试剂[D 2 ] 3 a / [D 2 ] 3 b进行的机理研究表明，这些单氟甲基化反应是通过亲电取代途径进行的。
• CuI/<scp>l</scp>-Proline-Catalyzed Coupling Reactions of Aryl Halides with Activated Methylene Compounds
  作者：Xiaoan Xie、Guorong Cai、Dawei Ma

  DOI：10.1021/ol0518838

  日期：2005.10.1

  [reaction: see text] The arylation of ethyl acetoacetate, ethyl benzoyl acetate, and diethyl malonate under the catalysis of CuI/L-proline in DMSO proceeds smoothly at 40-50 degrees C in the presence of Cs2CO3 to provide the 2-aryl-1,3-dicarbonyl compounds in good yields. Both aryl iodides and aryl bromides are compatible with these reaction conditions.

  [反应：请参见文本]在DMSO中CuI / L-脯氨酸的催化下，在Cs2CO3存在下，在40-50℃下，乙酰乙酸乙酯，苯甲酸乙酯和丙二酸二乙酯的芳基化反应顺利进行，从而提供了2-芳基- 1,3-二羰基化合物，收率高。芳基碘化物和芳基溴化物都与这些反应条件相容。
• Novel Mesoionic Insecticidal Compound
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US20200017490A1

  公开（公告）日：2020-01-16

  The purpose of the present invention is to provide a mesoionic compound, which exhibits an improved controlling effect on various harmful organisms, or a salt thereof. A mesoionic compound represented by formula (1) (wherein: R 1 is selected from a hydrogen atom, etc.; R 2 represents an optionally substituted phenyl group; R 3 is selected from a hydrogen atom, etc.; R 4 is selected from a hydrogen atom, etc.; R 5 is selected from an optionally substituted ethylene group, etc.; and X is selected from an oxygen atom, etc.) or a salt thereof.

  本发明的目的是提供一种嵌环离子化合物，其在各种有害生物上表现出改进的控制效果，或其盐。由式（1）表示的嵌环离子化合物（其中：R1选自氢原子等；R2代表可选择取代的苯基团；R3选自氢原子等；R4选自氢原子等；R5选自可选择取代的乙烯基团等；X选自氧原子等）或其盐。