3-(2,2,2-三氟乙氧基)-1-丙烯 | 1524-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2,2,2-三氟乙氧基)-1-丙烯
• 中文别名: 烯丙基2,2,2-三氟乙基醚
• 英文名称: allyl 2,2,2-trifluoroethyl ether
• 英文别名: 3-(2,2,2-trifluoroethoxy)prop-1-ene
• CAS: 1524-54-5
• 化学式: C₅H₇F₃O
• mdl: MFCD01727348
• 分子量: 140.105
• InChiKey: NOTCQEKRIPQPAW-UHFFFAOYSA-N

物化性质

• 沸点：
  54-59
• 密度：
  1.089 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT, FLAMMABLE
• 危险品标志：
  F,Xi
• 危险类别码：
  R10
• 危险品运输编号：
  UN 3271
• 海关编码：
  2909199090
• 安全说明：
  S16,S23,S36

反应信息

• 作为反应物：
  描述：

  3-(2,2,2-三氟乙氧基)-1-丙烯 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 4-(5-((2,2,2-trifluoroethoxy)methyl)-4,5-dihydroisoxazol-3-yl)aniline
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Isoxazoline and Isoxazole Group

  摘要：

  Twenty-two new benzoylphenylureas containing isoxazoline and the isoxazole group were designed and synthesized, and their structures were characterized by (1)H NMR and elemental analysis (or FIRMS). The larvicidal activities against Oriental armyworm, mosquito, and diamondback moth of the new compounds were evaluated. Compounds I-1 and III-1 showed nearly the same level of insecticidal activity against Oriental armyworm as commercial insecticide Flucycloxuron and surprisingly exhibited much higher larvicidal activities against diamondback moth than Flucycloxuron.

  DOI：

  10.1021/jf200395g
• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 3-溴丙烯 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 反应 16.0h， 以74%的产率得到3-(2,2,2-三氟乙氧基)-1-丙烯
  参考文献：
  名称：

  Synthesis of model organosiloxanes containing perfluoroether side-chains

  摘要：

  一系列有机三硅氧烷[(Me3SiO)2MeSi(CH2)nO(CH2)mRf]，其中（n = 3，m = 1，Rf = CF3；n = 3，m = 2，Rf = C4F9，C6F13，C8F17，C10F21，C7F15；n = 5，m = 1，Rf = CF3；n = 10，m = 0，Rf = C3HF6；n = 10，m = 1，Rf = CF3）已经通过[Pt(环辛二烯)Cl2]催化的氢硅化反应制备，反应物为七甲基三硅氧烷和CH2CH(CH2)n−2O(CH2)mRf。产率取决于烯链长度和Rf基团的支化程度。在涉及CH2CHCH2OCH2CF3的反应中，检测到了异构体产物[(Me3SiO)2MeSi(CH2)3OCH2CF3]和[(Me3SiO)2MeSiCH(Me)CH2OCH2CF3]。

  DOI：

  10.1039/b001376p

文献信息

• Rate and Product Studies on the Solvolyses of Allyl Chloroformate
  作者：Han Joong Koh、Suk Jin Kang

  DOI：10.5012/bkcs.2012.33.12.4117

  日期：2012.12.20

  The solvolysis rate constants of allyl chloroformate ($CH_2=CHCH_2OCOCl$, 3) in 30 different solvents are well correlated with the extended Grunwald-Winstein equation, using the $N_T$ solvent nucleophilicity scale and $Y_Cl}$ solvent ionizing scale, with the sensitivity values of $0.93\pm}0.05$ and $0.41\pm}0.02$ for l and m, respectively. These l and m values can be considered to support a $S_N2$ reaction pathway. The activation enthalpies ($\Delta}H^\neq}$) were 12.5 to 13.4 $kcal\cdot}mol^-1}$ and the activation entropies ($\Delta}S^\neq}$) were -34.4 to -37.3 $cal\cdot}mol^-1}\cdot}K^-1}$, which is also consistent with the proposed bimolecular reaction mechanism. The solvent kinetic isotope effect (SKIE, $k_MeOH}/k_MeOD}$) of 2.16 was also in accord with the $S_N2$ mechanism. The values of product selectivity (S) for the solvolyses of 3 in alcohol/water mixtures was 1.3 to 3.9, which is also consistent with the proposed bimolecular reaction mechanism.

  丙烯氯酸酯（$CH_2=CHCH_2OCOCl$, 3）在30种不同溶剂中的溶解反应速率常数与扩展的Grunwald-Winstein方程有很好的相关性，使用了 溶剂亲核性尺度和 溶剂电离尺度，其灵敏度值分别为<0.93\pm}0.05> 和<0.41\pm}0.02>。这些 l 和 m 值可以被视为支持 $S_N2$ 反应途径。活化焓（$\Delta}H^\neq}$）为12.5到13.4 $kcal\cdot}mol^-1}$，活化熵（$\Delta}S^\neq}$）为-34.4到-37.3 $cal\cdot}mol^-1}\cdot}K^-1}$，这也与所提议的双分子反应机制一致。溶剂动力学同位素效应（SKIE，$k_MeOH}/k_MeOD}$）为2.16，也符合 $S_N2$ 机制。在醇/水混合物中3的溶解反应的产物选择性值（S）为1.3到3.9，这也与所提议的双分子反应机制一致。
• A direct and rapid route to α,α-difluoroacylsilanes from trifluoroethanol
  作者：Christophe Audouard、Maxime R. Garayt、Erwan Kérourédan、Jonathan M. Percy、Hongli Yang

  DOI：10.1016/j.jfluchem.2005.01.005

  日期：2005.4

  α-Difluoroacylsilanes were synthesised directly from a range of allyl ethers of trifluoroethanol via dehydrofluorination/metallation procedures, followed by thermal [3,3]-sigmatropic rearrangement of the intermediate vinylmetals. The scope and limitations of ether synthesis and dehydrofluorination/metallation are described.

  α，α-二氟酰基硅烷是由一系列三氟乙醇的烯丙基醚通过脱氟化氢/金属化步骤直接合成的，然后对中间体乙烯基金属进行热[3,3]-σ重排。描述了醚合成和脱氟化氢/金属化的范围和限制。
• Synthesis of 2-substituted hydroquinone derivatives from 1,4-benzoquinone and allyl ethers
  作者：Kevin J. Kaurich、Paul A. Deck

  DOI：10.1016/j.tet.2018.01.048

  日期：2018.5

  B-Alkylpinacolboranes, derived from rhodium-catalyzed hydroboration of allyl ethers with pinacolborane, react with 1,4-benzoquinone under acidic, oxidizing conditions, to afford, after subsequent hydrogenation, 2-substituted hydroquinones in isolated, purified yields of about 50% based on 1,4-benzoquinone. The product hydroquinones have potential use as precursors to poly(arylene ether) and related

  由铑催化烯丙基醚与频哪醇硼烷进行氢硼烷基化反应制得的B-烷基萘烷硼烷在酸性氧化条件下与1,4-苯醌反应，在随后的氢化反应后，以约50％的分离纯化纯度提供2-取代的氢醌在1,4-苯醌上 产物氢醌具有用作聚亚芳基醚和相关芳族聚合物的前体的潜在用途。
• Correlation of the rates of solvolysis of allyl and benzyl arenesulphonates
  作者：Dennis N. Kevill、Thomas J. Rissmann

  DOI：10.1039/p29840000717

  日期：——

  Analysis of the specific rates of solvolysis of allyl arenesulphonates in terms of the extended Grunwald–Winstein equation indicates a marked dependence on both the solvent nucleophilicity (high l value) and the solvent ionizing power (highm value). As the charge delocalization in the leaving group increases, both l and m values fall. For allyl toluene-p-sulphonate solvolysis in 28 solvents at 50.0 °C

  用扩展的Grunwald-Winstein方程分析烯丙基芳烃磺酸盐的特定溶剂分解速率，表明对溶剂亲核性（高l值）和溶剂电离能力（高m值）都有明显的依赖性。随着离去基团中电荷离域的增加，l和m值均下降。对于在50.0°C下在28种溶剂中的烯丙基甲苯对磺酸酯溶剂分解，基于N KL和Y值的使用，l（0.83）和m（0.63）的值与0.90和0.90的当量值非常相似。先前报道的苄基甲苯-p为0.67-磺酸盐溶剂分解。考虑了相关的扩展的Grunwald–Winstein分析，并强调了在选择溶剂时需要多种选择。
• A Concise Route to Difluorinated Analogues of Cyclitols and Sugars
  作者：Jonathan Percy、Erwan Kérourédan、Giuseppe Rinaudo、Kuldip Singh

  DOI：10.1055/s-0028-1083240

  日期：2008.12

  Allyl ethers of trifluoroethanol are transformed to di­fluorinated analogues of deoxysugars via concise sequences involving dehydrofluorination/metallation, [3,3]-Claisen rearrangement, reduction, and RCM, affording cyclohexenediol substrates for dihydroxylation reactions.

  三氟乙醇的烯丙基醚通过涉及脱氟化氢/金属化、[3,3]-克莱森重排、还原和RCM的简明序列转化为脱氧糖的二氟化类似物，为二羟基化反应提供环己烯二醇底物。