but-3-enyl acrylate | 27819-07-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: but-3-enyl acrylate
• 英文别名: Homoallyl acrylate；but-3-enyl prop-2-enoate
• CAS: 27819-07-4
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: KHCUIHPWMFJSHA-UHFFFAOYSA-N

物化性质

• 沸点：
  154.4±19.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  but-3-enyl acrylate 在 Ru=CH-Ph(PCy₃)2Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以65%的产率得到5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h
• 作为产物：
  描述：

  2-vinyl-4,7-dihydro-[1,3]dioxepine 反应 0.02h， 生成 but-3-enyl acrylate
  参考文献：
  名称：

  Scissions sigmatropiques d'acétals non saturés

  摘要：

  DOI：

  10.1016/s0040-4020(01)97844-5

文献信息

• Cyclizations in the Addition of Alkylmercury Halides to Dienes and Enynes
  作者：Glen A. Russell、Chaozhong Li、Ping Chen

  DOI：10.1021/ja9601898

  日期：1996.1.1

  or CH2CHC(O)OC(Me)2CHCH2. The radicals t-BuCH2CH•C(O)C(Me)2(CH2)nCHCH2 cyclize mainly in the 6-endo mode for n = 1 and more rapidly in the 6-exo mode for n = 2, while the radicals t-BuCH2CH•C(O)OC(Me)2(CH2)nCHCH2 cyclize only in the exo mode for n = 0 or 1 but with a faster rate for 5-exo-cyclization. Gem-dimethyl substitution adjacent to the alkyl oxygen accelerates the 5-exo-cyclization of the ester

  将叔丁基卤化汞光刺激加成到 1,6-二烯和烯炔，包括 (CH2CHCH2)2X，其中 X = CH2、C(COEt)2、O 或 NCH2CHCH2，形成由 5-外环化产生的初级烷基卤化汞加合物自由基，t-BuCH2CH•CH2XCH2CHCH2。这些自由基过程的动力学链长度很低，在 Me2SO 中 35 °C 时的范围为 3-7。在光刺激下将 t-BuHgI 添加到 CH2CHP(O)(OR)OCH2CHCH2（R = H 或烯丙基）、CH2CHC(O)N(R)CH2CHCH2（R = Me、Ph 或 CH2CHCH2) 或 CH2CHC(O)OC(Me)2CHCH2。基团 t-BuCH2CH•C(O)C(Me)2(CH2)nCHCH2 在 n = 1 时主要以 6-endo 模式环化，在 n = 2 时以 6-exo 模式更快地环化，而基团 t-BuCH2CH•C(O)OC(Me)2(CH2)nCHCH2
• Synthesis of epoxy (meth)acrylic esters by selective epoxidation of unsaturated (meth)acrylic esters using the system H2O2 - Na2WO4 under phase transfer catalysis
  作者：Y. Fort、A. Olszewski-Ortar、P. Caubere

  DOI：10.1016/s0040-4020(01)90120-6

  日期：1992.1

  Selective epoxidation of unsaturated (meth)acrylic esters by various classical epoxidizing agents was investigated. It is shown that high selectivity and good yields are obtained by using the system H2O2 (20%) - Na2WO4 under phase transfer catalysis. Under these conditions, the rigorous control of the temperature and of the initial pH allows to prevent polymerization during these selective epoxidations

  研究了各种经典的环氧化剂对不饱和（甲基）丙烯酸酯的选择性环氧化。结果表明，在相转移催化下，通过使用H 2 O 2（20％）-Na 2 WO 4体系可以得到高选择性和高收率。在这些条件下，严格控制温度和初始pH值可防止在这些选择性环氧化过程中发生聚合。结果表明，环氧化的选择性取决于两个双键亲核性的差异。
• Nickel-Catalyzed Three-Component Reductive Alkylacylation of Electron-Deficient Activated Alkenes
  作者：Lin Wang、Chuan Wang

  DOI：10.1021/acs.orglett.0c03210

  日期：2020.11.20

  alkylacylation of electron-deficient activated alkenes with tertiary alkyl bromides and acid anhydrides. This method enables the efficient preparation of a variety of ketones with broad substrate scope and high functionality tolerance starting from simple precursors. On the basis of the preliminary mechanistic investigations, a catalytic cycle involving the synergistic interaction of nickel, zinc, and MgCl2

  在本文中，我们提出了缺电子活化烯烃与叔烷基溴化物和酸酐的镍催化三组分还原烷基酰化反应。该方法能够从简单的前体开始有效制备具有广泛底物范围和高功能耐受性的各种酮。在初步的机理研究的基础上，提出了涉及镍，锌和MgCl 2协同相互作用的催化循环作为主要反应途径。
• ELECTROLYTIC SOLUTION, ELECTROCHEMICAL DEVICE, LITHIUM ION SECONDARY BATTERY, AND MODULE
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20200280096A1

  公开（公告）日：2020-09-03

  An electrolyte solution containing a compound represented by the following formula (1): wherein R 101 and R 102 are the same as or different from each other and are each a hydrogen atom, a fluorine atom, or an alkyl group optionally containing a fluorine atom; and R 103 is an alkyl group or an organic group containing an unsaturated carbon-carbon bond. Also disclosed is an electrochemical device and lithium ion secondary battery including the electrolyte solution, and a module including the electrochemical device or lithium ion secondary battery.

  一种电解质溶液，包含由以下化学式（1）表示的化合物：其中R101和R102彼此相同或不同，分别为氢原子、氟原子或含有氟原子的烷基基团；R103为烷基基团或含有不饱和碳-碳键的有机基团。还公开了包括该电解质溶液的电化学器件和锂离子二次电池，以及包括电化学器件或锂离子二次电池的模块。
• Fast and unprecedented chemoselective hydroformylation of acrylates with a fluoropolymer ligand in supercritical CO2
  作者：Yulai Hu、Weiping Chen、Anna M. Banet Osuna、Jon A. Iggo、Jianliang Xiao

  DOI：10.1039/b201166b

  日期：2002.3.21

  A fluorous polymeric phosphine, when combined with supercritical CO2 (scCO2) and rhodium, effects fast and highly chemoselective hydroformylation of acrylates, one of the least reactive olefins in hydroformylation reactions.

  氟聚合物膦与超临界CO2（scCO2）和铑结合使用时，可实现丙烯酸酯的快速且高度化学选择性的加氢甲酰化，丙烯酸酯是加氢甲酰化反应中反应性最低的烯烃之一。