methyl 2-(3-(trifluoromethyl)phenyl)acrylate | 89744-95-6

• 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: methyl 2-(3-(trifluoromethyl)phenyl)acrylate
• 英文别名: 2-[3-(Trifluoromethyl)phenyl]acrylic acid methyl ester；methyl 2-[3-(trifluoromethyl)phenyl]prop-2-enoate
• CAS: 89744-95-6
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: LAZZIHALYQRTQT-UHFFFAOYSA-N

物化性质

• 沸点：
  269.1±40.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(trifluoromethyl)phenyl)acrylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (3-trifluoromethyl-phenyl)-acrylic acid
  参考文献：
  名称：

  铑（III）催化的CH活化/碳原子插入/丢失重排序列可高效合成螺氧杂吲哚吡咯酮。

  摘要：

  描述了铑（III）催化的简单烯烃与重氮恶吲哚的多米诺环化反应，以得到螺恶吲哚吡咯烷酮产物。可以将这种反应正式地看做是异常串联CH活化，卡宾插入，洛森重排和亲核加成过程的结果。药物分子的后期多样化进一步证明了该反应的潜在效用。

  DOI：

  10.1002/anie.201906589
• 作为产物：
  描述：

  间三氟甲基苯乙酸 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 2-(3-(trifluoromethyl)phenyl)acrylate
  参考文献：
  名称：

  铑（III）催化的CH活化/碳原子插入/丢失重排序列可高效合成螺氧杂吲哚吡咯酮。

  摘要：

  描述了铑（III）催化的简单烯烃与重氮恶吲哚的多米诺环化反应，以得到螺恶吲哚吡咯烷酮产物。可以将这种反应正式地看做是异常串联CH活化，卡宾插入，洛森重排和亲核加成过程的结果。药物分子的后期多样化进一步证明了该反应的潜在效用。

  DOI：

  10.1002/anie.201906589

文献信息

• [EN] 3- HETEROARYL SUBSTITUTED 5-TRIFLUOROMETHYL OXADIAZOLES AS HISTONE DEACETYLASE 6 (HDAC6) INHIBITORS<br/>[FR] 5-TRIFLUOROMÉTHYL-OXADIAZOLES SUBSTITUÉS PAR UN 3-HÉTÉROARYLE À TITRE D'INHIBITEURS D'HISTONE DÉSACÉTYLASE 6 (HDAC6)
  申请人：MERCK SHARP & DOHME

  公开号：WO2017222952A1

  公开（公告）日：2017-12-28

  The present invention is directed to substituted 5-trifluoromethyl oxadiazole compounds of generic formula (I) (I) or a pharmaceutically acceptable salt thereof. In particular, the invention is directed to a class of heteroaryl substituted 5-trifluoromethyl oxadiazole compounds of formula I which may be useful as HDAC6 inhibitors for treating cellular proliferative diseases, including cancer, neurodegenerative diseases, such as schizophrenia and stroke, as well as other diseases.

  本发明涉及通式(I)的取代5-三氟甲基噁二唑化合物或其药用可接受的盐。具体而言，本发明涉及一类杂环取代的通式I的5-三氟甲基噁二唑化合物，可能作为HDAC6抑制剂用于治疗细胞增殖性疾病，包括癌症、精神分裂症和中风等神经退行性疾病，以及其他疾病。
• Synthesis of 2-arylacrylic esters from aryl methyl ketones via Wittig reaction/singlet oxygen ene reaction
  作者：Sangjoon Park、Dongsik Yang、Kyoung Tae Kim、Heung Bae Jeon

  DOI：10.1016/j.tetlet.2011.09.127

  日期：2011.12

  has been developed for the synthesis of 2-arylacrylic esters from the corresponding aryl methyl ketones via Wittig reaction and singlet oxygen ene reaction. Wittig reaction to aryl methyl ketones with (methoxymethyl)triphenylphosphonium chloride in basic condition afforded the methyl enol ethers, and then 2-arylacrylic esters were obtained by singlet oxygen ene reaction, followed by tosylation and

  已经开发了一种有效的合成方法，用于通过Wittig反应和单线态氧烯反应从相应的芳基甲基酮合成2-芳基丙烯酸酯。在碱性条件下，与（甲氧基甲基）三苯基氯化在Wittig上与芳基甲基酮反应，得到甲基烯醇醚，然后通过单线态氧烯反应得到2-芳基丙烯酸酯，然后甲苯磺酸化并在一锅中消除为甲基烯醇醚。良品率高。
• Control of Site-Selectivity in Hydrogen Atom Transfer by Electrostatic Interaction: Proximal-Selective C(sp³)–H Alkylation of 2-Methylanilinium Salts Using a Decatungstate Photocatalyst
  作者：Jialin Zeng、Takeru Torigoe、Yoichiro Kuninobu

  DOI：10.1021/acscatal.2c00278

  日期：2022.3.4

  C(sp3)–H alkylation of 2-methylanilinium salts via radical intermediates was developed. The anionic decatungstate photocatalyst ([W10O32]4–) interacts with the ammonium group of the substrate through electrostatic interaction and selectively abstracts a hydrogen atom from the proximal benzylic carbon atom under UV irradiation. A variety of 2-methylanilinium salts reacted with electron-deficient alkenes

  开发了通过自由基中间体对 2-甲基苯胺盐进行位点选择性 C(sp 3 )-H 烷基化。阴离子十钨酸盐光催化剂（[W 10 O 32 ] 4-）通过静电相互作用与底物的铵基相互作用，并在紫外线照射下选择性地从近端苄基碳原子中提取一个氢原子。多种 2-甲基苯胺盐与缺电子烯烃反应。烷基化产物通过 C-N 键的断裂成功地转化为芳基碘化物，并通过分子内环化成功地转化为四氢苯并氮杂酮衍生物。机理研究清楚地表明 [W 10 O 32 ] 4–和铵基。
• A Phosphine-Catalyzed Regioselective [3+2] Cycloaddition of Ethyl 5,5-Diarylpenta-2,3,4-trienoate with Aromatic Aldehydes and α,β-Unsaturated Carbonyl Compounds
  作者：Lu-Feng Wang、Xiao-Ping Cao、Zi-Fa Shi、Peng An、Hak-Fun Chow

  DOI：10.1002/adsc.201301000

  日期：2014.11.3

  AbstractTributylphosphine‐catalyzed regioselective [3+2] cycloadditions between ethyl 5,5‐diarylpenta‐2,3,4‐trienoate 1 and various aromatic aldehydes 2 to produce a wide variety of polysubstituted 2,5‐dihydrofurans 3, and between 1 and β‐unsubstituted α,β‐unsaturated carbonyl compounds 5 to give polysubstituted cyclopentenes 6 with a quaternary carbon center, are reported. In both cases the reaction partners approach each other via the sterically less hindered orientation to afford the target products in excellent regioselectivity. The reaction mechanism involved first the generation of a zwitterionic intermediate between the butatriene 1 and PBu3. For the formation of 2,5‐dihydrofurans 3, the preferred cyclization mode encompassed the nucleophilic attack of the α‐position of butatriene to the aldehydic carbon of 2, followed by the ring closure between the aldehydic oxygen of 2 and the γ‐position of butatriene, which is the first report of a normal [3+2] cycloaddition between cumulenes and aldehydes. For the formation of cyclopentenes 6, the reaction involved attack of the γ‐position of the butatriene to the electron‐deficient β‐position of the α,β‐unsaturated carbonyl compounds 5, followed by the ring closure between the α‐position of 5 and the α‐position of butatriene, which shows a different regioselectivity to the previously reported [3+2] cycloadditions between butatriene and olefins.magnified image