(5-methylfuran-2-yl)(phenyl)methanol | 81779-39-7

• 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-methylfuran-2-yl)(phenyl)methanol
• 英文别名: (5-methylfuran-2-yl)phenylmethanol；5-methylfuran-2-yl(phenyl)methanol；α-phenylfurfuryl alcohol；5-methyl-2-furylbenzyl alcohol；(5-methyl-furan-2-yl)-phenyl-methanol；5-Methyl-2-furylphenylcarbinol；(5-Methylfuran-2-yl)-phenylmethanol
• CAS: 81779-39-7
• 化学式: C₁₂H₁₂O₂
• mdl: MFCD03211617
• 分子量: 188.226
• InChiKey: YZEUHKZUSVTLNV-UHFFFAOYSA-N

物化性质

• 沸点：
  279.3±35.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-methylfuran-2-yl)(phenyl)methanol 在 氧气 、 rose bengal 、 二甲基硫 作用下， 以 甲醇 、 dichlorometane 为溶剂， 反应 15.0h， 生成 5-hydroxy-5-methyl-2(5H)-furanone
  参考文献：
  名称：

  Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-exo-brevicomin

  摘要：

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.

  DOI：

  10.1021/ol200027f
• 作为产物：
  描述：

  5-甲基呋喃醛 、 溴苯 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (5-methylfuran-2-yl)(phenyl)methanol
  参考文献：
  名称：

  Catalytic Formal Benzylic C–H Bond Functionalization of 2,5-Dialkylfuran Derivatives with Ferrocenyl Alcohols as Alkylation Reagents

  摘要：

  The inert benzylic C-H bond of pi-electron-rich heteroaromatic 2,5-dialkylfuran derivatives was conveniently functionalized with ferrocenyl alcohols as alkylation reagents under catalytic acidic conditions at room temperature, which features chemo- and regiospecificity, mild and metallic catalyst free conditions, and environmental benignity.

  DOI：

  10.1021/acs.orglett.8b03701

文献信息

• Copper-Catalyzed Ring Opening of Furans as a Concise Route to Polysubstituted Furans under Mild Conditions
  作者：Biaolin Yin、Huiyue Yu、Zhengrong Li、Weiqiang Zhong、Wenxiang Gu

  DOI：10.1055/s-0032-1317683

  日期：——

  polysubstituted furans were synthesized from furan derivatives involving copper-catalyzed ring opening of the furan ring. This synthetic method possesses the advantages of readily available starting materials, mild reaction conditions, and short steps. A range of polysubstituted furans were synthesized from furan derivatives involving copper-catalyzed ring opening of the furan ring. This synthetic

  摘要 从涉及呋喃环的铜催化的开环的呋喃衍生物合成了一系列多取代的呋喃。该合成方法具有容易获得的原料，温和的反应条件和步骤短的优点。 从涉及呋喃环的铜催化的开环的呋喃衍生物合成了一系列多取代的呋喃。该合成方法具有容易获得的原料，温和的反应条件和步骤短的优点。
• An entry to polysubstituted furans via the oxidative ring opening of furan ring employing NBS as an oxidant
  作者：Huiyue Yu、Weiqiang Zhong、Tingyu He、Wenxiang Gu、Biaolin Yin

  DOI：10.1016/j.tetlet.2012.12.085

  日期：2013.3

  A class of polysubstituted functionalized furans was synthesized efficiently starting from readily available furans involving the oxidative ring opening of the furan rings using NBS as an oxidant. The reaction proceeded through a sequence of oxidative dearomatization of the furan ring/spirocyclization/aromatization.

  从容易获得的呋喃开始，使用NBS作为氧化剂，从涉及呋喃环氧化环开环的呋喃开始，有效地合成了一类多取代的官能化呋喃。反应通过呋喃环的氧化脱芳香化/螺环化/芳香化的顺序进行。
• Di- and triheteroarylalkanes via self-condensation and intramolecular Friedel–Crafts type reaction of heteroaryl alcohols
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1039/c3ob41945b

  日期：——

  diheteroarylmethanes and 1,3-diheteroarylpropenes has been developed via Yb(III)-catalyzed sequential self-condensation of 2-furfuryl (or 2-thienyl or 3-indolyl) alcohols followed by intramolecular Friedel–Crafts type reaction and elimination of an aldehyde. This method offers a powerful entry and a potential alternative to the traditional synthesis of diheteroarylalkanes, which are precursors to the synthesis

  通过Yb（III）催化2-糠基（或2-噻吩基或3-吲哚基）醇的顺序自缩合反应，然后进行分子内Friedel-Crafts型反应，开发了一种有效的合成方法，用于二杂芳基甲烷和1,3-二杂芳基丙烯。消除醛。该方法为传统的二杂芳基烷烃的合成提供了有力的途径和潜在的替代方法，后者是几种有趣的杂芳基化合物的合成的前体，更重要的是生物燃料的合成。
• Taming furfuryl cations for the synthesis of privileged structures and novel scaffolds
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1039/c3ob40814k

  日期：——

  Furfuryl cations are generated via a highly efficient bismuth-catalyzed reaction of furfuryl alcohols. This systematic study provides insight on the reactivity profile of furfuryl cations towards nucleophilic substitution reactions. Novel C–C, C–N, C–O and C–S bond forming reactions of furfuryl cations have been developed, thus providing access to a diverse array of building blocks for further manipulations.

  糠醇正离子通过一种高效率的铋催化糠醇反应生成。这项系统研究揭示了糠醇正离子在亲核取代反应中的反应活性概况。开发了糠醇正离子的新的C-C、C-N、C-O和C-S键形成反应，从而为更深入的分子操作提供了各种多样化的构建模块。
• One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
  作者：Petrakis N. Chalikidi、Taimuraz T. Magkoev、Andrey V. Gutnov、Oleg P. Demidov、Maxim G. Uchuskin、Igor V. Trushkov、Vladimir T. Abaev

  DOI：10.1021/acs.joc.1c00733

  日期：2021.7.16

  Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or

  已经开发了两种从容易获得的苯甲醇及其杂环类似物合成取代鏻盐的方法。所开发的方案是互补的：发现将醇、三甲基溴化甲硅烷和三苯基膦直接混合在 1,4-二恶烷中，然后在 80 °C 下加热对酸敏感底物（例如水杨醇或糠醇）更有效作为仲苯甲醇，而包括顺序添加三甲基甲硅烷基溴和三苯基膦的一锅法可以为带有电中性或吸电子取代基的苯甲醇提供更高的产率。