1-(furan-2-yl)-2-(isochroman-1-yl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(furan-2-yl)-2-(isochroman-1-yl)ethanone
• 英文别名: 2-(3,4-dihydro-1H-isochromen-1-yl)-1-(furan-2-yl)ethanone
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RAKQRYDLSPMDET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基呋喃 、 异色满 在 四溴化碳 作用下， 以 neat (no solvent) 为溶剂， 反应 48.0h， 以72%的产率得到1-(furan-2-yl)-2-(isochroman-1-yl)ethanone
  参考文献：
  名称：

  Catalytic amounts of CBr₄ mediated dehydrogenative coupling of isochromans with aromatic ketones

  摘要：

  在存在催化量的CBr₄（一种无金属介质）的情况下，异色酮与酮发生了意外的氧化脱氢偶联反应，构建了新的C^sp3–C^sp3键。这些反应是在简单的无溶剂氧化条件下进行的。

  DOI：

  10.1039/c4cc09922b

文献信息

• Copper(II) catalyzed cross-dehydrogenative coupling of cyclic benzylic ethers with simple carbonyl compounds by Na2S2O8
  作者：Xinhui Pan、Qingwen Hu、Wenfang Chen、Xigong Liu、Bin Sun、Zhouli Huang、Ziyu Zeng、Liguo Wang、Dan Zhao、Mei Ji、Lei Liu、Hongxiang Lou

  DOI：10.1016/j.tet.2014.03.074

  日期：2014.5

  Copper(II) catalyzed cross-dehydrogenative coupling of cyclic benzylic ethers with a variety of simple carbonyl compounds mediated by Na2S2O8 is developed. The scope of carbonyl components is broad, including simple aldehydes as well as ketones. The use of Na2S2O8 as the oxidant for the CDC reaction is attractive based on economical and environmental factors.

  开发了铜（II）催化的环状苄醚与各种由Na 2 S 2 O 8介导的简单羰基化合物的交叉脱氢偶联。羰基成分的范围很广，包括简单的醛以及酮。基于经济和环境因素，使用Na 2 S 2 O 8作为CDC反应的氧化剂是有吸引力的。
• Decarboxylative Alkylation of<i>β</i>-Keto Acids with Isochromans under Oxidative Conditions
  作者：Yan Chen、Shi-Kai Tian

  DOI：10.1002/cjoc.201200994

  日期：2013.1

  An unprecedented decarboxylative alkylation reaction of β‐keto acids with isochromans has been developed under oxidative conditions. A range of β‐keto acids smoothly undergo decarboxylative alkylation with isochromans in the presence of 2,2,6,6‐tetramethylpiperdine‐1‐oxoammonium hexafluorophosphate to give structurally diverse 1‐acylmethylisochromans in moderate to excellent yields with extremely high

  在氧化条件下，β-酮酸与异色团发生了前所未有的脱羧烷基化反应。在2,2,6,6-四甲基哌啶-1-氧代铵六氟磷酸酯的存在下，一系列β-酮酸能顺利地与异色团进行脱羧烷基化反应，从而以适中至优异的产率提供结构多样的1-酰基甲基异色烷，并具有极高的区域选择性。
• Oxidative Alkylation of Cyclic Benzyl Ethers with Malonates and Ketones Using Oxygen as the Terminal Oxidant
  作者：Chao-Jun Li、Woo-Jin Yoo、Camille Correia、Yuhua Zhang

  DOI：10.1055/s-0028-1087376

  日期：——

  A simple oxidative alkylation of cyclic benzyl ethers with malonatesand ketones was developed using a mixture of Cu(OTf) 2 ,InCl 3 , and NHPI as catalyst under an atmospheric pressureof oxygen.

  使用Cu(OTf) 2 、InCl 3 和NHPI 的混合物作为催化剂，在氧气大气压下，开发了环状苄基醚与丙二酸酯和酮的简单氧化烷基化反应。
• Manganese Dioxide–Methanesulfonic Acid Promoted Direct Dehydrogenative Alkylation of sp³ C–H Bonds Adjacent to a Heteroatom
  作者：Xigong Liu、Bin Sun、Zhiyu Xie、Xiaojun Qin、Lei Liu、Hongxiang Lou

  DOI：10.1021/jo4000674

  日期：2013.4.5

  A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). The employment of the combination of MnO2 and CH3SO3H is attractive on the basis of economical and environmental issues.
• DDQ-Mediated Direct Cross-Dehydrogenative-Coupling (CDC) between Benzyl Ethers and Simple Ketones
  作者：Yuhua Zhang、Chao-Jun Li

  DOI：10.1021/ja060050p

  日期：2006.4.5

  A direct Cross-Dehydrogenative-Coupling (CDC) between benzyl ethers and simple ketones was developed without using any metal catalyst. By using DDQ, various benzyl ethers and simples ketones were coupled together directly to form beta-alkoxyl ketones efficiently. A mechanism in which the DDQ serves the double roles of an oxidizing agent and an organomediator was proposed.