(5-methyl-2-furyl)triphenylmethane

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (5-methyl-2-furyl)triphenylmethane
• 英文别名: triphenyl(5-methyl-2-furyl)methane；2-methyl-5-tritylfuran；5-methyl-2-tritylfuran
• 化学式: C₂₄H₂₀O
• mdl: MFCD00552217
• 分子量: 324.422
• InChiKey: CFXYODWEJPFMJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基呋喃 、 三苯基甲醇 在 五氟苯硼酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以98%的产率得到(5-methyl-2-furyl)triphenylmethane
  参考文献：
  名称：

  Organocatalyzed Friedel–Crafts arylation of benzylic alcohols

  摘要：

  Electron-rich aromatic and heteroaromatic rings are functionalized directly with a variety of benzylic alcohols under mild conditions. The reaction is catalyzed by commercially available pentafluorophenylboronic acid, which is stable under ambient conditions and recoverable. The reaction itself is highly atom economical and produces water as the only byproduct. A Friedel-Crafts mechanism is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.151

文献信息

• Friedel-Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers
  作者：Anna Lielpetere、Aigars Jirgensons

  DOI：10.1002/ejoc.202000568

  日期：2020.8.9

  Friedel–Crafts alkylation of electron rich arenes can be achieved by stabilized carbenium ions which are generated by single cell anodic oxidation of stannylmethyl ethers at low potential. The use of NaHCO3 as an additive ensures close‐to‐neutral conditions enabling the reaction with arenes bearing acid‐sensitive groups such as O‐TBS, O‐Tr, O‐MOM, O‐THP.

  富电子芳烃的Friedel-Crafts烷基化可通过稳定的碳氧离子实现，该离子由低电位的苯乙烯甲基甲醚的单细胞阳极氧化产生。使用碳酸氢钠的3作为添加剂确保贴近中性条件使得能够与芳烃带有酸敏感基团，如反应Ó -TBS，ö -Tr，ö -MOM，ö -THP。
• Organocatalytic Friedel–Crafts Benzylation of Heteroaromatic and Aromatic Compounds via an SN1 Pathway
  作者：Hiyoshizo Kotsuki、Naruhisa Watanabe、Aoi Matsugi、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.1055/s-0033-1340343

  日期：——

  The Friedel-Crafts-type benzylation of various -excessive heteroaromatic and aromatic compounds with trityl or benzhydryl halides was efficiently promoted by a thiourea catalyst. This is a novel example of thiourea catalysis of aromatic alkylation by way of an S(N)1 pathway.
• Furylcyclohexenones. 1. Synthesis and properties of 3- and 5-furyl-6-ethoxycarbonylcyclohexenones
  作者：E. B. Usova、L. I. Lysenko、G. D. Krapivin、V. G. Kul'nevich

  DOI：10.1007/bf01164783

  日期：1996.5
• Reaction of cyclic ?-ketoalcohols with trityl perchlorate
  作者：E. B. Usova、G. D. Krapivin、L. I. Lysenko、V. G. Kul'nevich

  DOI：10.1007/bf00532043

  日期：1993.11
• Organocatalyzed Friedel–Crafts arylation of benzylic alcohols
  作者：J. Adam McCubbin、Oleg V. Krokhin

  DOI：10.1016/j.tetlet.2010.02.151

  日期：2010.5

  Electron-rich aromatic and heteroaromatic rings are functionalized directly with a variety of benzylic alcohols under mild conditions. The reaction is catalyzed by commercially available pentafluorophenylboronic acid, which is stable under ambient conditions and recoverable. The reaction itself is highly atom economical and produces water as the only byproduct. A Friedel-Crafts mechanism is proposed. (C) 2010 Elsevier Ltd. All rights reserved.