5-methoxy-2,2,3-trimethyl-2,3-dihydrobenzo[b]furan

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-methoxy-2,2,3-trimethyl-2,3-dihydrobenzo[b]furan
• 英文别名: 5-methoxy-2,2,3-trimethyl-2,3-dihydrobenzofuran；5-methoxy-2,2,3-trimethyl-3H-1-benzofuran
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: HKZRYQBBZWZURM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-2-丁烯 、 4-甲氧基苯酚 在 lithium perchlorate 、 溶剂黄146 作用下， 以 硝基甲烷 为溶剂， 以97%的产率得到5-methoxy-2,2,3-trimethyl-2,3-dihydrobenzo[b]furan
  参考文献：
  名称：

  脂族烯烃荧光标记的电化学活性交联反应

  摘要：

  尽管交联反应是整合两个或多个功能或特性的宝贵工具，但由于传质困难，电化学合成在交联反应中的应用受到限制。因此，本研究的主要目的是探索由共价键形成引发的电化学交联系统，以构建荧光探针。第二个目的是将探针应用于不溶性靶标。为了实现这些目标，将电化学活性酚衍生物和脂族烯烃结合使用以形成多环化合物。通过[3 + 2]环化反应形成的几种二氢苯并呋喃衍生物表现出荧光。此外，C键形成。

  DOI：

  10.1002/chem.201103630

文献信息

• Electrochemically Active Cross-Linking Reaction for Fluorescent Labeling of Aliphatic Alkenes
  作者：Shokaku Kim、Kumi Hirose、Jumpei Uematsu、Yuzuru Mikami、Kazuhiro Chiba

  DOI：10.1002/chem.201103630

  日期：2012.5.14

  these goals, a combination of electrochemically active phenol derivatives and aliphatic alkenes were employed to form polycyclic compounds. Several of the dihydrobenzofuran derivatives formed through [3+2] cyclization reactions exhibited fluorescence. Furthermore, this approach allowed the effective modification of alkene‐modified silica gel with electrochemically active species, which enables the construction

  尽管交联反应是整合两个或多个功能或特性的宝贵工具，但由于传质困难，电化学合成在交联反应中的应用受到限制。因此，本研究的主要目的是探索由共价键形成引发的电化学交联系统，以构建荧光探针。第二个目的是将探针应用于不溶性靶标。为了实现这些目标，将电化学活性酚衍生物和脂族烯烃结合使用以形成多环化合物。通过[3 + 2]环化反应形成的几种二氢苯并呋喃衍生物表现出荧光。此外，C键形成。
• Dihydrobenzofuran Synthesis by an Anodic [3 + 2] Cycloaddition of Phenols and Unactivated Alkenes
  作者：Kazuhiro Chiba、Miho Fukuda、Shokaku Kim、Yoshikazu Kitano、Masahiro Tada

  DOI：10.1021/jo9908243

  日期：1999.10.1
• An Oxidative Carbon−Carbon Bond Formation System in Cycloalkane-Based Thermomorphic Multiphase Solution
  作者：Shokaku Kim、Satoko Noda、Kanako Hayashi、Kazuhiro Chiba

  DOI：10.1021/ol8004408

  日期：2008.5.1

  A selective anodic oxidation system in which a carbocation intermediate is generated exclusively by use of a temperature-control led multiphase solution to separate the different stages of the reaction from each other and from the products is described. The formation of a thermomorphic middle layer in an electrolytic solution composed of c-Hex and LPC/MeNO2 results in enhanced interaction between aliphatic alkenes and polar unstable cation.
• Heterogeneous continuous flow synthetic system using cyclohexane-based multiphase electrolyte solutions
  作者：Yohei Okada、Tomohiko Yoshioka、Mikio Koike、Kazuhiro Chiba

  DOI：10.1016/j.tetlet.2011.07.007

  日期：2011.9

  The discovery that supporting electrolytes can be effectively confined in typical organic solvents in a c-Hex-based multiphase electrolyte solution has led to the development of a novel heterogeneous continuous flow synthetic system. PTFE fiber functions as a separation filter that can efficiently isolate the c-Hex phase from multiphase electrolyte solutions. This system has demonstrated both electrochemical solvating and carbon-carbon bond forming reactions. Hydrophobic substrates can be introduced into the reactor as c-Hex solutions, which are then electrochemically transformed into the target hydrophobic products that pass through the PTFE fiber as c-Hex solutions. (C) 2011 Elsevier Ltd. All rights reserved.
• Photocatalytic Cycloadditions Enabled by a Lithium Perchlorate/Nitromethane Electrolyte Solution
  作者：Shingo Nagahara、Hiroki Wakamatsu、Yohei Okada、Kazuhiro Chiba

  DOI：10.1002/ejoc.201801280

  日期：2018.12.19

  Photocatalytic cycloadditions involving carbon–carbon bond formation in the absence of an external sensitizer are described. The use of a lithium perchlorate/nitromethane electrolyte solution exhibiting remarkable Lewis acidity is the key for the successful transformations.

  描述了在没有外部敏化剂的情况下涉及碳-碳键形成的光催化环加成反应。使用显示出显着路易斯酸度的高氯酸锂/硝基甲烷电解质溶液是成功转化的关键。