5-(2-fluorophenyl)dihydrofuran-2(3H)-one | 1270585-14-2

• 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: 5-(2-fluorophenyl)dihydrofuran-2(3H)-one
• 英文别名: 5-(2-Fluorophenyl)oxolan-2-one；5-(2-fluorophenyl)oxolan-2-one
• CAS: 1270585-14-2
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: AMIZIQPVECOFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(2-氟苯基)丁酸 在 氢溴酸 、 (2-(N-methylbenzamido)phenyl)-l 3-iodanediyl diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以75%的产率得到5-(2-fluorophenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  苯胺型高价碘 (III) 用于通过含有 N-和 O-亲核试剂的烃的 C-H 键抽象进行分子内环化

  摘要：

  我们开发了一种制备（二乙酰氧基碘）-2-（N-烷基酰胺基）苯作为苯胺型高价碘 (III) 的方法。我们还通过 C−H 键提取实现了直接环化，例如 Hofmann-Löffler-Freytag 反应、直接胺化和直接内酯化，使用苯胺型高价碘 (III) 以高产率获得相应的产物。

  DOI：

  10.1002/adsc.202100316

文献信息

• MnO₂-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones
  作者：Lihuan Wu、Zhenming Zhang、Jianhua Liao、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c5cc08867d

  日期：——

  A new radical cyclization method for the formation of C(sp³)–C(sp³) and C–O bonds via MnO₂-promoted alkene carboesterification with anhydrides is developed.

  一种新的基于锰促进的烯烃碳酯化反应的C(sp3)-C(sp3)和C-O键的放射状环化方法被开发出来。
• Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids
  作者：Yufei Lu、Jing Li、Yue Zhu、Jiefeng Shen、Delong Liu、Wanbin Zhang

  DOI：10.1016/j.tet.2019.05.036

  日期：2019.6

  An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral γ-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral γ-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction

  已经开发了通过RuPHOX-Ru催化剂催化的芳酰基丙烯酸的不对称氢化，以高收率和高达93％的ee提供了相应的手性γ-内酯。该方法具有利用容易获得的底物的优点，因此扩大了所得手性γ-内酯的范围。此外，由于一步实现了C C和C O双键的还原，因此实现了高催化效率。目前的工作为广泛的手性γ-内酯的合成提供了另一种方便的途径。
• Low‐Impact Synthesis of γ‐Lactones Through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones
  作者：Maria Chiara Cabua、Viktoria Velichko、Luca Pilia、Davide Moi、Francesco Secci

  DOI：10.1002/ejoc.202400226

  日期：——

  A photocatalyzed oxidation of functionalized cyclobutanones to access γ-lactones has been performed in acetonitrile at room temperature, using 9,10-anthraquinone as catalysts in the presence of TFA. The process furnish good to excellent yields of the desired compounds in 4–16 h reaction and after simple filtration of the recyclable catalyst.

  在室温下，使用 9,10-蒽醌作为催化剂，在 TFA 存在下，在乙腈中进行了官能化环丁酮的光催化氧化以获得 γ-内酯。该工艺在 4-16 小时的反应中以及在对可回收催化剂进行简单过滤后，可提供良好至优异的所需化合物收率。
• Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes
  作者：Sanjeewa K. Rodrigo、Hairong Guan

  DOI：10.1021/jo301790q

  日期：2012.9.21

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.
• Aniline‐Type Hypervalent Iodine(III) for Intramolecular Cyclization via C−H Bond Abstraction of Hydrocarbons Containing N‐ and O‐Nucleophiles
  作者：Yuna Nishiguchi、Katsuhiko Moriyama

  DOI：10.1002/adsc.202100316

  日期：2021.7

  We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C−H bond abstraction, such as the Hofmann-Löffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields.

  我们开发了一种制备（二乙酰氧基碘）-2-（N-烷基酰胺基）苯作为苯胺型高价碘 (III) 的方法。我们还通过 C−H 键提取实现了直接环化，例如 Hofmann-Löffler-Freytag 反应、直接胺化和直接内酯化，使用苯胺型高价碘 (III) 以高产率获得相应的产物。