2,3-二氢-5-三氟乙酰基吡喃 | 109317-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,3-二氢-5-三氟乙酰基吡喃
• 英文名称: 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone
• 英文别名: 5-trifluoroacetyl-3,4-dihydro-2H-pyran；1-(3,4-dihydro-2H-pyran-5-yl)-2,2,2-trifluoroethanone
• CAS: 109317-74-0
• 化学式: C₇H₇F₃O₂
• mdl: MFCD00975077
• 分子量: 180.127
• InChiKey: CTFORTFPVUYECO-UHFFFAOYSA-N

物化性质

• 沸点：
  64.6 °C(Press: 10.5 Torr)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2,3-二氢-5-三氟乙酰基吡喃 在 氢氧化钾 、 水 作用下， 以 苯 为溶剂， 反应 7.0h， 以100%的产率得到2,3-二氢-吡喃-5-羧酸
  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 3-(2,2,2-trifluoro-acetyl)-tetrahydro-pyran-2-yl ester 以 四氯化碳 为溶剂， 反应 120.0h， 生成 2,3-二氢-5-三氟乙酰基吡喃
  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

• Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions
  作者：Marco Thomas Passia、Jan-Hendrik Schöbel、Niklas Julian Lentelink、Khai-Nghi Truong、Kari Rissanen、Carsten Bolm

  DOI：10.1039/d1ob01912k

  日期：——

  TBS-protected or NH-sulfonimidamides react with β-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to give 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-Functionalized products can be obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value

  TBS 保护的或N H-磺酰亚胺酰胺在无溶剂机械化学条件下与 β-烷氧基乙烯基三氟甲基酮反应生成 3-三氟甲基取代的三维 1,2,6-噻二嗪 1-氧化物。C4-官能化产物可以通过从环状烯酮和最初形成的杂环的溴化开始获得。通过改变pH值和有氧条件下的储存来研究产物的稳定性。
• 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。
• 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。
• Reaction of Alkyl and Aryl Grignard Reagents with Trifluoroacetyldihydropyrans and Other Cyclic β-Alkoxy-α,β-unsaturated Trifluoromethylketones
  作者：John M Mellor、Gill Reid、Afaf H El-Sagheer、El-Sayed H El-Tamany

  DOI：10.1016/s0040-4020(00)00975-3

  日期：2000.12

  β-unsaturated trifluoromethylketones by 1,4-addition to give as the major products, for example, cis-2,3-disubstituted tetrahydropyrans. In most examples ring opening leads to stereoselective formation of rearranged hemiketals as minor products. Under other conditions with 2,2,2-trifluoro-1-(2-ethoxy-3,4-dihydro-2H-5-pyranyl)-1-ethanone stereoselective ring opening leads to acyclic aldehydes, as minor products

  烷基和芳基格氏试剂通过加成1,4-与环状β-烷氧基-α，β-不饱和三氟甲基酮反应生成主要产物，例如，顺式-2,3-二取代的四氢吡喃。在大多数例子中，开环导致作为次要产物的重排半酮的立体选择性形成。在其他条件下，带有2,2,2-三氟-1-（2-乙氧基-3,4-二氢-2 H -5-吡喃基）-1-乙酮的立体选择开环会生成无环醛，作为次要产物，并通过通过添加更多当量的格利雅试剂，是通往一系列二醇的主要途径。在较高温度下不存在其他格氏试剂的情况下，内部氢化物转移可提供无环酯。
• Haloacetylated enol ethers.<b>8</b>[12]. Reaction of β-alkoxyvinyl trihalomethyl ketones with guanidine hydrochloride. Synthesis of 4-trihalomethyl-2-aminopyrimidines
  作者：Nilo Zanatta、Maria de F. M. Cortelini、Marcos J. S. Carpes、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1002/jhet.5570340226

  日期：1997.3

  In this work the results of the reaction of β-alkoxyvinyl trihalomethyl ketones 1, 2a-e, with guanidine hydrochloride are reported. Depending on the ketone 1 or 2 and the conditions under which the reactions were carried out, 4-trihalomethyl-2-amino pyrimidines, β-alkoxyvinyl carboxylic acids, or β-acetal carboxylic esters were obtained.

  在这项工作中，报道了β-烷氧基乙烯基三卤代甲基酮1、2a-e与盐酸胍的反应结果。根据酮1或2和进行反应的条件，获得4-三卤甲基-2-氨基嘧啶，β-烷氧基乙烯基羧酸或β-缩醛羧酸酯。