ethyl 4,4,4-trifluoro-2-formylbutanoate | 142820-58-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4,4,4-trifluoro-2-formylbutanoate
• 英文别名: 4,4,4-trifluoro-2-formyl-butyric acid ethyl ester
• CAS: 142820-58-4
• 化学式: C₇H₉F₃O₃
• 分子量: 198.142
• InChiKey: BFPJWUJORNQROW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,4,4-trifluoro-2-formylbutanoate 在 劳森试剂 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以44%的产率得到4-(2,2,2-Trifluoroethyl)dithiole-3-thione
  参考文献：
  名称：

  Synthesis and structure–activity relationships study of dithiolethiones as inducers of glutathione in the SH-SY5Y neuroblastoma cell line

  摘要：

  Parkinson's disease is a neurodegenerative disorder that involves the degeneration of nigrostriatal dopaminergic neurons. Elevated levels of reactive oxygen species have been shown to deplete cellular levels of the ubiquitous antioxidant glutathione, leading to oxidative stress and eventual neuronal cell death. Dithiolethiones, a class of sulfur-containing heterocyclic molecules, have been shown to induce cellular production of glutathione in a variety of tissues, but have not been extensively evaluated in neurons. Herein, we report the synthesis and preliminary structure-activity relationships study of several substituted dithiolethiones. Three molecules were identified (D3T, CPDT, and 2d) that potently induced cellular glutathione in the SH-SY5Y neuroblastoma cell line. Furthermore, these compounds were found to provide neuroprotection in the 6-hydroxydopamine model of neurotoxicity. This study suggests that dithiolethione-mediated neuroprotection may have potential as a disease-modifying antiparkinsonian therapy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.005
• 作为产物：
  描述：

  ethyl 3-chloro-2-formyl-4,4,4-trifluorobut-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以91%的产率得到ethyl 4,4,4-trifluoro-2-formylbutanoate
  参考文献：
  名称：

  Synthesis of γγγ-trifluorocarbonyl compounds

  摘要：

  Gammagammagamma-trifluorocarbonyl compounds are easily obtained in a good yield by introduction of the 1,1,1-trifluoroethyl moiety (CF3-CH2-) on the alpha-methylene group of a ketone.

  DOI：

  10.1016/s0040-4039(00)74726-5

文献信息

• [EN] SUBSTITUTED PHENOXYMETHYL DIHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF<br/>[FR] PHÉNOXYMÉTHYL-DIHYDRO-OXAZOLOPYRIMIDINONES SUBSTITUÉES, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2011034832A1

  公开（公告）日：2011-03-24

  The present invention relates to a series of substituted phenoxymethyl dihydro oxazolopyrimidinones of formula (I) defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, cognition deficit disorders, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列被取代的苯氧甲基二氢噁唑吡咯嘧啶酮化合物，其化学式为（I）。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR）的调节剂，特别是mGluR2受体。因此，本发明的化合物可用作药物制剂，特别是在治疗和/或预防各种中枢神经系统疾病（CNS）方面，包括但不限于急性和慢性神经退行性疾病、精神病、认知缺陷疾病、癫痫、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐。
• Efficient Synthesis of New Fluorinated Building Blocks by means of Hydroformylation
  作者：Lidia Fanfoni、Lisa Diab、Tomas Smejkal、Bernhard Breit

  DOI：10.2533/chimia.2014.371

  日期：——

  Hydroformylation of fluorinated alkenes is an efficient method for the preparation of fluorinated functionalized building blocks for the synthesis of biologically active target structures. In this article we summarize known hydroformylation reactions of fluorinated olefins and we add new results from our research groups. Particular attention is paid to the remarkable influence of organofluorine substituents

  氟化烯烃的加氢甲酰化是制备用于合成生物活性靶结构的氟化官能化结构单元的有效方法。在本文中，我们总结了氟化烯烃的已知加氢甲酰化反应，并增加了我们研究组的新结果。特别注意有机氟取代基对加氢甲酰化反应的催化剂活性，区域选择性和立体选择性的显着影响。
• PYRIMIDINONE DERIVATIVES AND THEIR USE IN THE TREATMENT OF ATHEROSCLEROSIS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1337517B1

  公开（公告）日：2008-11-26
• Synthesis and structure–activity relationships study of dithiolethiones as inducers of glutathione in the SH-SY5Y neuroblastoma cell line
  作者：Dennis A. Brown、Swati Betharia、Jui-Hung Yen、Quang Tran、Hitesh Mistry、Kari Smith

  DOI：10.1016/j.bmcl.2014.10.005

  日期：2014.12

  Parkinson's disease is a neurodegenerative disorder that involves the degeneration of nigrostriatal dopaminergic neurons. Elevated levels of reactive oxygen species have been shown to deplete cellular levels of the ubiquitous antioxidant glutathione, leading to oxidative stress and eventual neuronal cell death. Dithiolethiones, a class of sulfur-containing heterocyclic molecules, have been shown to induce cellular production of glutathione in a variety of tissues, but have not been extensively evaluated in neurons. Herein, we report the synthesis and preliminary structure-activity relationships study of several substituted dithiolethiones. Three molecules were identified (D3T, CPDT, and 2d) that potently induced cellular glutathione in the SH-SY5Y neuroblastoma cell line. Furthermore, these compounds were found to provide neuroprotection in the 6-hydroxydopamine model of neurotoxicity. This study suggests that dithiolethione-mediated neuroprotection may have potential as a disease-modifying antiparkinsonian therapy. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of γγγ-trifluorocarbonyl compounds
  作者：AndréJ. Laurent、Stanislaw Lesniak

  DOI：10.1016/s0040-4039(00)74726-5

  日期：1992.12

  Gammagammagamma-trifluorocarbonyl compounds are easily obtained in a good yield by introduction of the 1,1,1-trifluoroethyl moiety (CF3-CH2-) on the alpha-methylene group of a ketone.