ethyl 3-hydroxy-2-methylene-3-(3-trifluoromethylphenyl)propionate

• 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: ethyl 3-hydroxy-2-methylene-3-(3-trifluoromethylphenyl)propionate
• 英文别名: Ethyl 2-[hydroxy-[3-(trifluoromethyl)phenyl]methyl]prop-2-enoate
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: YQKOIGRHLWGRIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-2-methylene-3-(3-trifluoromethylphenyl)propionate 在 4-二甲氨基吡啶 、 iron(III)-acetylacetonate 、 乙醇 、 苯硅烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 (E)-5-(ethoxycarbonyl)-3,3-dimethyl-6-(3-(trifluoromethyl)phenyl)hex-5-en-1-yl 4-methoxybenzoate
  参考文献：
  名称：

  Fe（III）催化未活化烯烃与森田-贝利斯-希尔曼加合物的水解反应

  摘要：

  描述了铁（III）催化未活化的烯烃与森田-贝利斯-希尔曼加合物通过铁催化的过程的加氢反应。在此方案中，各种烯烃（包括单，二和三取代的烯烃）都可以顺利转化为结构多样化的肉桂酸酯。有趣的是，当使用含羟基的烯烃时，可以迅速组装各种内酯。而且，该协议可以应用于天然产物的后期功能化。

  DOI：

  10.1021/acs.orglett.8b00108
• 作为产物：
  描述：

  3-三氟甲基苯甲醇 、 丙烯酸乙酯 在 硫酰氟 、 potassium carbonate 、 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以83%的产率得到ethyl 3-hydroxy-2-methylene-3-(3-trifluoromethylphenyl)propionate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel arylpropionic esters for the treatment of acute kidney injury

  摘要：

  Acute kidney injury (AKI) is associated with a strong inflammatory response, and inhibiting the response effectively prevents or ameliorates AKI. A series of novel arylpropionic esters were designed, synthesized and evaluated their biological activity in LPS-stimulated RAW264.7 cells. Novel arylpropionic esters bearing multi-functional groups showed significant anti-inflammatory activity, in which, compound 13b exhibited the most potent activity through dose-dependent inhibiting the production of nitric oxide (NO, IC₅₀ = 3.52 μM), TNF-α and IL-6 (84.1% and 33.6%, respectively), as well as suppressing the expression of iNOS, COX-2 and TLR4 proteins. In C57BL/6 mice with cisplatin-induced AKI, compound 13b improved kidney function, inhibited inflammatory development, and reduced pathological damage of kidney tissues. In brief, this arylpropionic ester scaffold may be developed as anti-inflammatory agents.

  DOI：

  10.1016/j.bioorg.2020.104455

文献信息

• Bifunctional Lewis Base Catalyzed Asymmetric <i>N</i>-Allylic Alkylation of 2-Hydroxypyridines
  作者：Fei-Ruo Zhang、Fanshu Cao、Kui Liu、Yi-Ping He、Gen Luo、Zhi-Shi Ye

  DOI：10.1021/acs.orglett.2c03207

  日期：2022.12.2

  A chiral Lewis base catalyzed enantioselective N-allylic alkylation of 2-hydroxypyridines and MBH carbonates is documented, affording a convenient access to N-alkylated 2-pyridones with up to 99% ee and 99% yield. Experimental and computational studies have revealed that the strong hydrogen bond interaction between the chiral Lewis base catalyst and 2-hydroxypyridines plays a crucial role in this reaction

  记录了手性路易斯碱催化的 2-羟基吡啶和 MBH 碳酸酯的对映选择性N-烯丙基烷基化，提供了一种方便地获得N-烷基化 2-吡啶酮的途径，其 ee 高达 99%，产率高达 99%。实验和计算研究表明，手性路易斯碱催化剂与 2-羟基吡啶之间的强氢键相互作用对该反应的反应性、化学选择性和对映选择性起着至关重要的作用。
• Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita–Baylis–Hillman Adducts
  作者：Jifeng Qi、Jing Zheng、Sunliang Cui

  DOI：10.1021/acs.orglett.8b00108

  日期：2018.3.2

  An Fe(III)-catalyzed hydroallylation of unactivated alkenes with Morita–Baylis–Hillman adducts via an Fe-catalyzed process is described. A variety of alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified cinnamates in this protocol. Interestingly, when the hydroxyl-containing alkenes were used, various lactones could be rapidly assembled. Moreover

  描述了铁（III）催化未活化的烯烃与森田-贝利斯-希尔曼加合物通过铁催化的过程的加氢反应。在此方案中，各种烯烃（包括单，二和三取代的烯烃）都可以顺利转化为结构多样化的肉桂酸酯。有趣的是，当使用含羟基的烯烃时，可以迅速组装各种内酯。而且，该协议可以应用于天然产物的后期功能化。
• Design, synthesis and biological evaluation of novel arylpropionic esters for the treatment of acute kidney injury
  作者：Jiawei Zuo、Shi-Meng Wang、Xia Jiang、Mengxin Cao、Ziwen Zhang、Tianlu Shi、Hua-Li Qin、Wenjian Tang

  DOI：10.1016/j.bioorg.2020.104455

  日期：2020.12

  Acute kidney injury (AKI) is associated with a strong inflammatory response, and inhibiting the response effectively prevents or ameliorates AKI. A series of novel arylpropionic esters were designed, synthesized and evaluated their biological activity in LPS-stimulated RAW264.7 cells. Novel arylpropionic esters bearing multi-functional groups showed significant anti-inflammatory activity, in which, compound 13b exhibited the most potent activity through dose-dependent inhibiting the production of nitric oxide (NO, IC₅₀ = 3.52 μM), TNF-α and IL-6 (84.1% and 33.6%, respectively), as well as suppressing the expression of iNOS, COX-2 and TLR4 proteins. In C57BL/6 mice with cisplatin-induced AKI, compound 13b improved kidney function, inhibited inflammatory development, and reduced pathological damage of kidney tissues. In brief, this arylpropionic ester scaffold may be developed as anti-inflammatory agents.