2-(2-chlorophenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one | 1381845-87-9

• 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-(2-chlorophenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
• 英文别名: 2-(o-chlorophenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；2-(2-chlorophenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；2-(2-chlorophenyl)-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
• CAS: 1381845-87-9
• 化学式: C₁₄H₁₃ClO₂
• 分子量: 248.709
• InChiKey: JZRUQWPTKFXGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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 potassium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.17h， 生成 2-(2-chlorophenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
  参考文献：
  名称：

  Metal-Catalyzed Thermal Reactions of Cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes

  摘要：

  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.

  DOI：

  10.1021/jo502611x

文献信息

• An organocatalyzed highly regioselective one-pot approach to the synthesis of tetrahydrobenzofuranones
  作者：Ruchi Chawla、Atul K. Singh、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2012.04.101

  日期：2012.6

  An organocatalyzed highly regioselective synthesis of substituted tetrahydrobenzofuran-4-ones based on the ring opening followed by cyclization of epoxides with enamines of 1,3-cyclohexanediones in a domino fashion is described. It is a high yielding (74-93%) synthetic protocol tolerant to a wide range of substrates. Ambient temperature, organocatalytic approach, atom-economy, and formation of water as the only by-product are some of the attractive features of the present methodology. (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.