2-methyl-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-methyl-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
• 英文别名: 2-Methyl-2-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one；2-methyl-2-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；2-Methyl-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4-one
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: NMLUJGPVNPTDFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,3-环己二酮 在 氢氧化钾 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.17h， 生成 2-methyl-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
  参考文献：
  名称：

  2-苯基碘-1,3-二氧杂环己烷亚甲基的[3 + 2]-环加成反应：熔融二氢呋喃衍生物的简便合成

  摘要：

  衍生自1,3-环己二酮的碘鎓碘化物2与乙腈，二硫化碳和p，p'-二甲氧基硫代二苯甲酮在Cu（acac）2催化下进行热[3 + 2]-环加成反应，形成相应的5元杂环和烯烃分别。光化学反应2与各种烯烃和二烯反应形成二氢呋喃衍生物，这是潘尼硫醚A，B和戊烯合成的关键中间体。

  DOI：

  10.1016/s0040-4039(98)01997-2

文献信息

• [3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives
  作者：Amalia Asouti、Lazaros P. Hadjiarapoglou

  DOI：10.1016/s0040-4039(98)01997-2

  日期：1998.12

  Iodonium ylide 2, derived from 1,3-cyclohexadione, undergoes thermal [3+2]-cycloaddition with acetonitrile, carbon disulfide and p, p′-dimethoxythiobenzophenone with Cu(acac)2 catalysis to form the corresponding 5-membered heterocycles and alkene respectively. Photochemically 2 reacts with various alkenes and dienes to form dihydrofuran derivatives, key intermediates for paniculide A, B and pentalene

  衍生自1,3-环己二酮的碘鎓碘化物2与乙腈，二硫化碳和p，p'-二甲氧基硫代二苯甲酮在Cu（acac）2催化下进行热[3 + 2]-环加成反应，形成相应的5元杂环和烯烃分别。光化学反应2与各种烯烃和二烯反应形成二氢呋喃衍生物，这是潘尼硫醚A，B和戊烯合成的关键中间体。
• Manganese(iii) acetate mediated radical reactions in the presence of an ionic liquid
  作者：Gregory Bar、Andrew F. Parsons、C. Barry Thomas

  DOI：10.1039/b103544b

  日期：——

  A new, mild and practical method for conducting manganese(III)-mediated radical reactions, which lead to the formation of carbon–carbon bonds, has been developed using the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]).

  利用离子液体 1-丁基-3-甲基咪唑四氟硼酸盐（[bmim][BF4]），我们开发出了一种新的、温和而实用的方法，用于进行锰（III）介导的自由基反应，从而形成碳-碳键。
• Fused dihydrofurans from the one-pot, three-component reaction of 1,3-cyclohexanedione, iodobenzene diacetate and alkenes
  作者：Dimitra Kalpogiannaki、Catherine-Irene Martini、Aggeliki Nikopoulou、John A. Nyxas、Vassiliki Pantazi、Lazaros P. Hadjiarapoglou

  DOI：10.1016/j.tet.2012.12.006

  日期：2013.2

  The one-pot, three-component reactions of substituted 1,3-cyclohexanediones, iodobenzene diacetate and alkenes, under photochemical activation, yields fused dihydrofuran derivatives in good yield via the in situ formation of iodonium ylides. (C) 2012 Elsevier Ltd. All rights reserved.
• Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans
  作者：Li-Na Guo、Shun Wang、Lin-Ye He

  DOI：10.1055/s-0034-1378806

  日期：——

  A potassium persulfate promoted tandem radical addition/cyclization of 1,3-dicarbonyl compounds with styrenes has been developed. This transition-metal-free procedure provides an efficient approach to a diverse set of substituted dihydrofurans in moderate to good yields.
• Metal-Catalyzed Thermal Reactions of Cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes
  作者：Alexandra-Eleni Bosnidou、Dimitra Kalpogiannaki、Sofia Karanestora、John A. Nixas、Lazaros P. Hadjiarapoglou

  DOI：10.1021/jo502611x

  日期：2015.1.16

  A cyclic beta-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh-2(OAc)(4) catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.