2-vinyltetrahydrofuran | 1072-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-vinyltetrahydrofuran
• 英文别名: 2-Ethenyloxolane
• CAS: 1072-60-2
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: XIXWTBLGKIRXOP-UHFFFAOYSA-N

物化性质

• 沸点：
  109 °C
• 密度：
  0.8939 g/cm3(Temp: 21 °C)
• 保留指数：
  1090.9

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2-vinyltetrahydrofuran 在 titanium(IV) isopropylate 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 1-bromooct-4-ene
  参考文献：
  名称：

  摘要：

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).

  DOI：

  10.1023/a:1026047515568
• 作为产物：
  描述：

  四氢吡喃-2-甲醇 在 吡啶 、 氢氧化钾 、 双氧水 、 溶剂黄146 、 iron(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-vinyltetrahydrofuran
  参考文献：
  名称：

  Taillez, Bernard; Bertrand, Michele Paula; Surzur, Jean-Marie, Journal of the Chemical Society. Perkin transactions II, 1983, p. 547 - 554

  摘要：

  DOI：

文献信息

• Heterocycle Synthesis Based on Allylic Alcohol Transposition Using Traceless Trapping Groups
  作者：Youwei Xie、Paul E. Floreancig

  DOI：10.1002/anie.201402010

  日期：2014.5.5

  Allylic alcohols undergo transposition reactions in the presence of Re2O7 whereby the equilibrium can be dictated by trapping one isomer with a pendent electrophile. Additional ionization can occur when the trapping group is an aldehyde or ketone, thus leading to cyclic oxocarbenium ion formation. Terminating the process through bimolecular nucleophilic addition into the intermediate provides a versatile

  烯丙醇在Re 2 O 7的存在下进行转座反应，从而可以通过用一种亲电亲和剂捕获一种异构体来控制平衡。当捕获基团是醛或酮时，可能会发生其他电离，从而导致形成环氧碳鎓离子。通过将双分子亲核加成至中间物来终止该过程，为合成各种含氧杂环化合物提供了一种通用的方法。了解序列中各步骤的相对速率会导致设计反应，从而创建多个具有良好至极佳控制水平的立体中心。
• Regioselective Ring-Cleavage Reaction of Tetrahydrofurans and Tetrahydropyrans Accompanied by Carbon–Carbon Bond Formation
  作者：Akira Oku、Yukio Homoto、Toshiro Harada

  DOI：10.1246/cl.1986.1495

  日期：1986.9.5

  Various 2-substituted tetrahydrofurans and tetrahydropyrans were cleaved regioselectively accompanied by a simultaneous carbon–carbon bond formation at the highly substituted α carbon atom by using the reagent system of titanium tetrachloride and ally- (or alkynyl-)silanes.

  通过使用四氯化钛和烯丙基-（或炔基-）硅烷的试剂系统，各种2-取代的四氢呋喃和四氢吡喃被区域选择性地裂解，同时在高度取代的α碳原子上形成碳-碳键。
• Ligand-enabled gold-catalyzed 1,2-heteroarylation of alkenes
  作者：Akash G. Tathe、Chetan C. Chintawar、Vivek W. Bhoyare、Nitin T. Patil

  DOI：10.1039/d0cc03707a

  日期：——

  By adopting the interplay between ligand-enabled Au(I)/Au(III) catalysis and the unique π-activation mode of gold complexes, a highly coveted 1,2-heteroarylation of alkenes has been accomplished. The present ligand-enabled approach not only circumvents the requirement for strong sacrificial oxidants or photocatalysts but also operates under mild reaction conditions by utilizing simple and non-prefunctionalized

  通过采用配体使能的Au（I）/ Au（III）催化与金络合物独特的π活化模式之间的相互作用，已实现了令人垂涎的烯烃1,2-杂芳基化。本发明的使配体成为可能的方法不仅克服了对强牺牲氧化剂或光催化剂的需求，而且通过利用简单的和未预官能化的芳基偶联伙伴在温和的反应条件下操作。
• Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis
  作者：Jun-Qi Zhang、Yunkui Liu、Xing-Wang Wang、Liming Zhang

  DOI：10.1021/acs.organomet.9b00400

  日期：2019.10.28

  The synthesis and characterization of the chiral bifunctional NHC ligands based on the imidazo[1,5-a]pyridine (ImPy) scaffold are described. These ligands possess a fluxional biaryl axis and a chiral center. The configurational stability of the biaryl axis in their gold(I) complexes is investigated. The application of these axially chiral ImPy-based AuCl complexes in a series of gold catalysis is explored

  描述了基于咪唑并[1,5- a ]吡啶（ImPy）支架的手性双官能NHC配体的合成和表征。这些配体具有通量的联芳基轴和手性中心。研究了联芳基轴在其金（I）配合物中的构型稳定性。探索了这些轴向手性基于ImPy的AuCl配合物在一系列金催化中的应用，并观察到了不同程度的不对称诱导。在大多数情况下，配体（a S，R）-L8-H的环己基指向反应位点，因此发挥不对称空间影响在不对称诱导中更有效。
• Stereochemical requirements of acetylenic retro-ene transition states
  作者：Alfred Viola、John J. Collins

  DOI：10.1039/c39800001247

  日期：——

  Retro-ene reactions of acetylenic and olefinic substrates differ in the stereochemical requirements of their respective transition states; reactions of olefins proceed via a chair-like (or boat-like) configuration while those of acetylenes require planarity.

  炔属和烯烃类底物的逆烯反应在其各自过渡态的立体化学要求上有所不同。烯烃的反应通过椅子样（或船形）构型进行，而乙炔的反应则需要平面性。