3-tert-butyl-4,4-difluorocyclohexa-2,5-dien-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-tert-butyl-4,4-difluorocyclohexa-2,5-dien-1-one
• 英文别名: 3-Tert-butyl-4,4-difluorocyclohexa-2,5-dien-1-one
• 化学式: C₁₀H₁₂F₂O
• 分子量: 186.201
• InChiKey: VQHKFTDLQXOVPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-叔丁基苯酚 在 triethylamine pentahydrogen fluoride salt 、 碳酸二甲酯 作用下， 反应 6.0h， 以68%的产率得到3-tert-butyl-4,4-difluorocyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Effective synthesis of difluorocyclohexadienones by electrochemical oxidation of phenols

  摘要：

  Electrochemical oxidation of phenols was examined using Et3N-5HF as the electrolyte and various electrodes. Carbon fiber cloth was found to be Suitable as the anode and a variety of phenols Could be converted to 4,4-difluorocyclohexadienone derivatives in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01440-5

文献信息

• Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions
  作者：Antoine Bienvenu、Audrey Barthelemy、Sarah Boichut、Bernard Marquet、Thierry Billard、Bernard R. Langlois

  DOI：10.1135/cccc20021467

  日期：——

  4-tert-Butylphenols can be easily transformed into 4-fluorophenols, provided that no coordinating moiety is present in 2-position, in a two step procedure under mild and safe conditions. The first step leads to 4-tert-butyl-4-fluorocyclohexa-2,5-dien-1-ones through an oxidative fluorination with [bis(trifluoroacetoxy)iodo]benzene and triethylamine tris(hydrofluoride), and is followed by an acid catalyzed aromatization with loss of isobutene. When extended to 4-tert-butylacetanilide, this method delivers 4-fluoroacetanilide in a single step but in a modest yield.

  4-tert-丁基酚可以在温和且安全的条件下，通过两步程序轻松转化为4-氟苯酚，前提是2位没有配位基团存在。第一步通过氧化氟化反应与[双(三氟乙酰氧)碘]苯和三乙胺三氢氟化物生成4-tert-丁基-4-氟环己-2,5-二烯酮，随后通过酸催化芳构化反应失去异丁烯。当将此方法扩展至4-tert-丁基乙酰苯胺时，该方法可以在单步中将其转化为4-氟乙酰苯胺，但产率较低。
• Effective synthesis of difluorocyclohexadienones by electrochemical oxidation of phenols
  作者：Tsuyoshi Fukuhara、Yuriko Akiyama、Norihiko Yoneda、Takahisa Tada、Shoji Hara

  DOI：10.1016/s0040-4039(02)01440-5

  日期：2002.9

  Electrochemical oxidation of phenols was examined using Et3N-5HF as the electrolyte and various electrodes. Carbon fiber cloth was found to be Suitable as the anode and a variety of phenols Could be converted to 4,4-difluorocyclohexadienone derivatives in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.