(E)-2-(4-(trifluoromethyl)styryl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(4-(trifluoromethyl)styryl)tetrahydrofuran
• 英文别名: 2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]oxolane
• 化学式: C₁₃H₁₃F₃O
• 分子量: 242.241
• InChiKey: SQBPBJUYCVMZTO-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-己炔-1-醇 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四(三苯基膦)钯 copper(l) iodide 、 (R,R)-2-exo-3-endo-bis(diphenylphosphino)bicyclo-[2.2.1]-heptane 、 三乙胺 、 苯甲酸 作用下， 以 苯 为溶剂， 反应 72.0h， 生成 (E)-2-(4-(trifluoromethyl)styryl)tetrahydrofuran
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes

  摘要：

  A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd-2(dba)(3)center dot CHCl3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 degrees C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.

  DOI：

  10.1021/jo0603835

文献信息

• Radical C(sp³)–H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis
  作者：Subhasis Paul、Joyram Guin

  DOI：10.1039/c7gc00840f

  日期：——

  enables selective incorporation of alkenyl, alkynyl and allyl functional groups into the C(sp3)–H bond under green reaction conditions is developed. The process is based on the catalytic formation of α-alkoxyl/α-amidyl radicals via the homolytic activation of the C(sp3)–H bond of ethers/amides with a catalytic amount of diarylketone in the presence of a household fluorescent light bulb. This simple reaction

  开发了一种有效的自由基加成/消除反应，该反应能够在绿色反应条件下将烯基，炔基和烯丙基官能团选择性地掺入C（sp 3）–H键中。该过程基于在家用荧光灯的存在下，通过催化量的醚/酰胺的C（sp 3）-H键与催化量的二芳基酮的均质活化，催化形成α-烷氧基/α-ami基自由基。。这种简单的反应方案具有良好的官能团耐受性，可扩展性，方便的试剂和操作系统。该方法的合成应用已通过天然产物和不同有价值的合成酮的制备得到证明。
• Visible-Light-Mediated Oxidative Decarboxylative Coupling of Cinnamic Acid Derivatives with Tetrahydrofuran
  作者：Zheng Liu、Leifeng Wang、Dong Liu、Zhigang Wang

  DOI：10.1055/s-0035-1560661

  日期：——

  A visible-light-mediated protocol for direct oxidative decarboxylative coupling of various cinnamic acid derivatives with tetrahydrofuran was developed, leading to simple preparations of a range of vinyltetrahydrofurans under operationally mild and convenient conditions.

  开发了一种可见光介导的各种肉桂酸衍生物与四氢呋喃直接氧化脱羧偶联的方案，从而在操作温和方便的条件下简单地制备了一系列乙烯基四氢呋喃。
• Photoinduced Pd-Catalyzed C_sp2–H/C_sp3–H Dehydrocoupling Reaction Employing Polyhaloaromatics as the Dehydrogenating Agent
  作者：Lin Chen、Kai Jiang、Guohui Zeng、Biaolin Yin

  DOI：10.1021/acs.orglett.2c03708

  日期：2022.12.16

  strategy for intermolecular cross-dehydrocoupling of Csp2–H bonds and Csp3–H bonds has been developed with the aid of photoinduced Pd catalysis. Polyhalogenated arenes can be used as the efficient dehydrogenating agent, which enables multifold transfer of carbon radical to avoid the production of stoichiometric or excess wasted arenes. In this strategy, substituted styrenes and N-arylacrylamides with simple

  在光诱导 Pd 催化的帮助下，已经开发了一种用于 C sp2 -H 键和 C sp3 -H 键的分子间交叉脱氢偶联的温和策略。多卤代芳烃可用作有效的脱氢剂，它可以实现碳自由基的多重转移，以避免产生化学计量或过量的废芳烃。在该策略中，取代的苯乙烯和N-芳基丙烯酰胺与简单的醚或酰胺作为偶联伙伴，以中等到良好的产率得到相应的内部烯烃和苯并内酰胺。
• Visible Light-Induced Direct S₀ → T_<i>n</i> Transition of Benzophenone Promotes C(sp³)–H Alkynylation of Ethers and Amides
  作者：Koki Matsumoto、Masaya Nakajima、Tetsuhiro Nemoto

  DOI：10.1021/acs.joc.0c01573

  日期：2020.9.18

  Benzophenone has an S-0 -> S-1 absorption band at 365 nm. However, the rarely reported S-0 -> T-n transition occurs upon irradiation at longer wavelengths. Herein, we employed benzophenone as a catalyst and exploited its S-0 -> T-n transition in C(sp(3))-H alkynylations with hypervalent iodine reagents. The selective benzophenone excitation prevented alkynylating reagent decomposition, enabling the reaction to proceed under mild conditions. The reaction mechanism was investigated by spectroscopic and computational studies.
• Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes
  作者：Nitin T. Patil、Léopold Mpaka Lutete、Huanyou Wu、Nirmal K. Pahadi、Ilya D. Gridnev、Yoshinori Yamamoto

  DOI：10.1021/jo0603835

  日期：2006.5.1

  A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd-2(dba)(3)center dot CHCl3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 degrees C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.