4-苯基-1-(四氢呋喃-2-基)丁烷-2-酮 | 1033863-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-苯基-1-(四氢呋喃-2-基)丁烷-2-酮
• 英文名称: 4-phenyl-1-(tetrahydrofuran-2-yl)butan-2-one
• 英文别名: 1-(Oxolan-2-yl)-4-phenylbutan-2-one
• CAS: 1033863-01-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: FXYRJXMGFCXKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氢氟酸 、 水 、 对甲苯磺酸 作用下， 以 环戊基甲醚 、 乙腈 为溶剂， 反应 24.0h， 生成 4-苯基-1-(四氢呋喃-2-基)丁烷-2-酮
  参考文献：
  名称：

  Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts

  摘要：

  Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalytic cycloetherification of epsilon-hydroxy-alpha,beta-unsaturated ketones mediated by cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.

  DOI：

  10.1021/ja207322d

文献信息

• Tandem Ruthenium-Catalyzed Redox Isomerization−O-Conjugate Addition: An Atom-Economic Synthesis of Cyclic Ethers
  作者：Barry M. Trost、Alicia C. Gutierrez、Robert C. Livingston

  DOI：10.1021/ol9007876

  日期：2009.6.18

  An atom-economical method for the convenient synthesis of tetrahydropyrans and tetrahydrofurans is reported. Enones and enals derived from the [IndRu(PPh3)2Cl]-catalyzed redox isomerization of primary and secondary propargyl alcohols undergo a subsequent intramolecular conjugate addition to provide cyclic ethers in excellent yields.

  报道了一种方便合成四氢吡喃和四氢呋喃的原子经济方法。衍生自 [IndRu(PPh 3 ) 2 Cl] 催化氧化还原异构化的伯和仲炔丙醇的烯酮和烯醛经过随后的分子内共轭加成以优异的产率提供环醚。
• Au(I)- and Pt(II)-Catalyzed Cycloetherification of ω-Hydroxy Propargylic Esters
  作者：Jef K. De Brabander、Bo Liu、Mingxing Qian

  DOI：10.1021/ol8008107

  日期：2008.6.1

  Depending on the nature of the metal catalyst, omega-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl(2)Pt(CH(2)CH(2))]2 (Zeise's dimer) will induce a propargylic substitution via an unprecedented S(N)2'-type allenic substitution from within

  取决于金属催化剂的性质，ω-羟基炔丙基乙酸酯在替代的环醚化歧管之间进行选择，以高产率生产官能化的杂环。AuCl催化氧杂环烯醇乙酸酯的形成，而[Cl（2）Pt（CH（2）CH（2））] 2（Zeise's二聚体）将通过前所未见的S（N）2'型烯丙基取代诱导炔丙基取代从螯合的方形平面阳离子Pt（II）络合物中获得。
• Organocatalytic Enantioselective Cycloetherifications Using a Cooperative Cation-Binding Catalyst
  作者：Amol P. Jadhav、Jeong-A Oh、In-Soo Hwang、Hailong Yan、Choong Eui Song

  DOI：10.1021/acs.orglett.8b02240

  日期：2018.9.7

  A highly enantioselective cycloetherification strategy for the straightforward synthesis of enantioenriched tetrahydrofurans, tetrahydropyrans, and oxepanes using Song’s cation-binding oligoEG catalyst and KF as the base is demonstrated. A wide range of ε-, ζ-, and η-hydroxy-α,β-unsaturated ketones were cyclized to the corresponding five-, six-, and seven-membered chiral oxacycles with high enantiopurity

  展示了一种高度对映体选择性的环醚化策略，该策略可使用Song的阳离子结合寡聚EG催化剂和KF作为碱直接合成富对映体的四氢呋喃，四氢吡喃和氧杂环丁烷。各种各样的ε-，ζ-和η-羟基-α，β-不饱和酮被环化成具有高对映体纯度的相应的五元，六元和七元手性氧杂环。这种非常成功的催化作用可归因于由手性催化剂，底物和KF原位生成的密闭超分子手性笼中的系统协同阳离子结合催化。
• Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View
  作者：Suzanne M. Opalka、Jeremy L. Steinbacher、Brandon A. Lambiris、D. Tyler McQuade

  DOI：10.1021/jo200838v

  日期：2011.8.19

  A thiourea/proline derivative-catalyzed synthesis of linear a-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.