2,3-二氢-4-三氟乙酰基呋喃 | 109317-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 2,3-二氢-4-三氟乙酰基呋喃
• 中文别名: 1-(4,5-二氢呋喃-3-基)-2,2,2-三氟-1-乙酮
• 英文名称: 4-trifluoroacetyl-2,3-dihydrofuran
• 英文别名: 1-(4,5-Dihydrofuran-3-yl)-2,2,2-trifluoroethan-1-one；1-(2,3-dihydrofuran-4-yl)-2,2,2-trifluoroethanone
• CAS: 109317-75-1
• 化学式: C₆H₅F₃O₂
• mdl: MFCD00728712
• 分子量: 166.1
• InChiKey: ZZZDLWOTMHJTDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  48.5 °C
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2,3-二氢-4-三氟乙酰基呋喃 在 氢氧化钾 、 水 作用下， 以 苯 为溶剂， 反应 5.0h， 以81%的产率得到4,5-二氢呋喃-3-甲酸
  参考文献：
  名称：

  A Convenient Synthetic Method for β-Alkoxy- and β-Phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids

  摘要：

  反δ-²-三卤乙酰乙烯基醚 1 很容易在苯中被湿氢氧化钾水解，从而以极好的收率生成相应的酸 2。这种合成方法也可用于环乙烯基醚 3 和 5，从而以较高的产率制得 4 和 6。

  DOI：

  10.1055/s-1986-31854
• 作为产物：
  描述：

  Trifluoro-acetic acid (2R,3S)-3-(2,2,2-trifluoro-acetyl)-tetrahydro-furan-2-yl ester 以 四氯化碳 为溶剂， 反应 23.0h， 生成 2,3-二氢-4-三氟乙酰基呋喃
  参考文献：
  名称：

  Addition-Elimination Reaction in the Trifluoroacetylation of Electron-Rich Olefins

  摘要：

  Reactions of electron-rich olefins such as vinyl ether 1 and vinyl sulfide 2 with trifluoroacetic anhydride in carbon tetrachloride at room temperature proceeded by the formation of addition products 7 and 8, respectively, which were identified as stable intermediates by H-1 NMR and IR spectra, eventually giving the, corresponding trifluoroacetylated olefins 5 and 6 as substitution products. These reactions were also observed in chloroform and dichloromethane in the absence. of base, such as pyridine. These results supported the addition-elimination mechanism. The processes of the addition and elimination were confirmed by the H-1 NMR spectrum and kinetic study which led to the following results: The addition products 7 and 8 were formed through a stepwise trans addition, and the trifluoroacetylated olefins 5 and 6 were self-catalytically formed from the addition products 7 and 8 through Ei, E2, or E1, depending on the stability of the cationic intermediates 3 and 4.

  DOI：

  10.1021/jo00116a045

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• Hepatitis C Virus Inhibitors
  申请人：Sin Ny

  公开号：US20080119461A1

  公开（公告）日：2008-05-22

  Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  抑制丙型肝炎病毒的抑制剂具有一般公式。包含这些化合物的组合物以及使用这些化合物抑制HCV的方法也被披露。
• New, simple, and efficient method for the synthesis of N-substituted 4-trifluoromethyl-5-(alkan-1-ol)-pyridin-2(1H)-imines
  作者：Mário A. Marangoni、Carlos E. Bencke、Helio G. Bonacorso、Marcos A.P. Martins、Nilo Zanatta

  DOI：10.1016/j.tetlet.2017.09.024

  日期：2017.10

  A new, simple, and efficient method for the synthesis a novel series of 1-substituted 4-(trifluoromethyl)-5-(alkan-1-ol)-pyridin-2(1H)-imines from the reaction of 3-(5,6-dihydro-4H-pyran-3-yl)-4,4,4-trifluorobut-2-enenitrile and 3-(4,5-dihydrofuran-3-yl)-4,4,4-trifluorobut-2-enenitrile with primary amines – is described. The products were obtained in 29–82% yield.

  一种新的，简单而有效的方法，可从3-（-）的反应中合成一系列新的1-取代的4-（三氟甲基）-5-（链烷-1-醇）-吡啶-2（1 H）-亚胺5,6-二氢-4 H-吡喃-3-基）-4,4,4-三氟丁-2-烯腈和3-（4,5-二氢呋喃-3-基）-4,4,4-三氟丁-描述了带有伯胺的2-腈。以29-82％的收率获得产物。
• Convenient One-Pot Synthesis of N-Substituted 3-Trifluoroacetyl Pyrroles
  作者：Nilo Zanatta、Ana Wouters、Leonardo Fantinel、Fabio da Silva、Rosemário Barichello、Pedro da Silva、Daniela Ramos、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-0028-1087821

  日期：——

  A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same

  提出了一种新的一锅法合成一系列新的 N-取代 3-三氟乙酰基吡咯。这些化合物是通过 3-三氟乙酰基-4,5-二氢呋喃与伯胺反应得到的，反应生成 1,1,1-三氟-3-(2-羟乙基)-4-烷基氨基丁-3-en-2-one中间体。在大多数情况下，这些中间体不够稳定，无法分离。因此，在同一反应容器中，它们直接被 PCC（科里试剂）氧化以提供 1,1,1-三氟-3-(2-乙醛)-4-烷基氨基丁-3-en-2-ones，其中在回流下进行分子内环化，以中等产率得到所需的 N-取代 3-三氟乙酰基吡咯。
• Reaction of Benzyl Grignard Reagents with Trifluoroacetyldihydropyrans and Other Cyclic β-Alkoxy-α,β-Unsaturated Trifluoromethylketones
  作者：Simon J Coles、John M Mellor、Afaf H El-Sagheer、Ezz El-Din M Salem、Reda N Metwally

  DOI：10.1016/s0040-4020(00)00976-5

  日期：2000.12

  Benzyl Grignard reagents react with cyclic β-alkoxy-α,β-unsaturated trifluoromethyl ketones by 1,2-addition to afford unsaturated allylic alcohols in high yield. The factors determining the balance between 1,2- and 1,4-addition to unsaturated ketones are discussed. The structures of major and minor products are established by single crystal X-ray diffraction studies.

  苄基格氏试剂通过加成1,2-与环状β-烷氧基-α，β-不饱和三氟甲基酮反应，以高收率得到不饱和烯丙基醇。讨论了确定不饱和酮中1,2-和1,4-加成之间平衡的因素。主要和次要产品的结构是通过单晶X射线衍射研究确定的。