2-(4-methylphenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one | 1381845-90-4

• 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-(4-methylphenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
• 英文别名: 2-(4-methylphenyl)-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
• CAS: 1381845-90-4
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: UEOOVHFLSROKEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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-(4-methylphenyl)spiro[2.5]octane-4,8-dione 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以97%的产率得到2-(4-methylphenyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
  参考文献：
  名称：

  酸催化的螺环丙烷的开环环化反应，用于2-芳基苯并呋喃骨架的构建：Cuspidan B的全合成

  摘要：

  摘要 在无金属条件下，环己烷-1,3-二酮-2-螺环丙烷的酸催化开环环化反应在室温下顺利进行，得到2-芳基-3,5,6,7-四氢-1-苯并呋喃-4 （2 H）-一的产率极高，而不会形成3-取代的异构体。所得产物通过合成上有用的2-芳基-2，3-二氢苯并呋喃中间体转化为2-芳基苯并呋喃衍生物。此外，通过使用本方法实现了cuspidan B的第一全合成。 在无金属条件下，环己烷-1,3-二酮-2-螺环丙烷的酸催化开环环化反应在室温下顺利进行，得到2-芳基-3,5,6,7-四氢-1-苯并呋喃-4 （2 H）-一的产率极高，而不会形成3-取代的异构体。所得产物通过合成上有用的2-芳基-2，3-二氢苯并呋喃中间体转化为2-芳基苯并呋喃衍生物。此外，通过使用本方法实现了cuspidan B的第一全合成。

  DOI：

  10.1055/s-0035-1561590

文献信息

• Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons
  作者：Yuta Onuki、Koga Yamazaki、Yuto Masuda、Takayuki Yakura、Hisanori Nambu

  DOI：10.1002/adsc.202300021

  日期：——

  In this study, regio- and diastereoselective ring-opening cyclization of spirocyclopropanes with phosphorus ylides stabilized by electron-withdrawing groups were developed. The reaction of various cyclohexane-1,3-dione-2-spirocyclopropanes with phosphorus ylides bearing alkoxycarbonyl groups proceeded smoothly without any additives to provide the corresponding 6,7-dihydroindan-4-ones in 32–87% yields

  在这项研究中，开发了螺环丙烷与吸电子基团稳定的磷叶立德的区域和非对映选择性开环环化反应。各种环己烷-1,3-二酮-2-螺环丙烷与带有烷氧基羰基的磷叶立德的反应在没有任何添加剂的情况下顺利进行，以32-87%的产率提供相应的6,7-二氢茚满-4-酮。环庚烷-1,3-二酮-2-螺环丙烷也用于该反应，产生相应的产物1,2,3,6,7,8-六氢薁-4-酮，产率52-67%。所得的[5.6]-和[5.7]-稠合碳环产物很容易通过氧化分别转化为高度取代的茚满和甘菊环。
• 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.
• 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.