2,2-dichloro-2-fluoro-1-(4-methoxyphenyl)ethanol | 16629-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2-dichloro-2-fluoro-1-(4-methoxyphenyl)ethanol
• 英文别名: 1-(4-Methoxy-phenyl)-2,2-dichlor-2-fluor-aethanol
• CAS: 16629-92-8
• 化学式: C₉H₉Cl₂FO₂
• 分子量: 239.074
• InChiKey: QGWQTHKOTTZBFK-UHFFFAOYSA-N

物化性质

• 沸点：
  127-128 °C(Press: 2 Torr)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-2-fluoro-1-(4-methoxyphenyl)ethanol 在 高碘酸 、 pyridinium chlorochromate 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以62%的产率得到2,2-dichloro-2-fluoro-1-(4-methoxyphenyl) ethanone
  参考文献：
  名称：

  用面包酵母制备各种α-氟代芳基酮的新合成路线及其对映选择性还原

  摘要：

  通过二氯氟甲基芳基醇的氧化获得高度亲电的二氯氟甲基芳基酮。随后使用甲醛合次硫酸氢钠（Rongalite）和还原性脱卤系统SnCl 2 / Al对这些酮进行脱氯，分别制得各种氟甲基芳基酮和氯氟甲基芳基酮。使用廉价的面包酵母不对称地还原这些氟化酮，可制得具有不同对映选择性的相应的氟甲基芳基醇。

  DOI：

  10.1016/j.tet.2006.11.019
• 作为产物：
  描述：

  2,2-dichloro-2-fluoro-1-(4-methoxyphenyl) ethanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2,2-dichloro-2-fluoro-1-(4-methoxyphenyl)ethanol
  参考文献：
  名称：

  1, 1-Diaryl- and 1-Aryl-2-chloro-2-fluoroethylenes

  摘要：

  DOI：

  10.1246/bcsj.40.1275

文献信息

• Addition of CFCl₃to Aromatic Aldehydes under Ultrasonic Irradiation
  作者：Sadao Tsuboi、Balaka Barkakaty、Yutaka Takaguchi

  DOI：10.1055/s-2006-926367

  日期：——

  Reductive addition of CFCl3 to aromatic aldehydes under the influence of activated aluminum powder and ultrasonic irradiation produced chlorofluoro carbinols in reasonable to excellent yields.

  在活性铝粉和超声波照射的影响下，CFCl3 与芳香醛的还原加成反应产生了氯氟甲醇，收率合理至优异。
• Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction
  作者：Balaka Barkakaty、Bandana Talukdar、Bradley Lokitz

  DOI：10.3390/molecules200815098

  日期：——

  cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In this report, we present a novel method for in situ Grignard reaction using magnesium powder and CFCl3 for synthesis of dichlorofluoromethyl aromatic alcohols.

  将三氯氟甲烷 (CFCl3) 合成改性为非挥发性和有用的氟化前体是一种经济高效且环境友好的策略，可安全消耗/破坏试剂的臭氧消耗潜力。在本报告中，我们提出了一种使用镁粉和 CFCl3 进行原位格氏反应合成二氯氟甲基芳香醇的新方法。
• A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine–bromine complexes
  作者：Zhen-Wu Mei、Takumi Omote、Mounir Mansour、Hiroyuki Kawafuchi、Yutaka Takaguchi、Anny Jutand、Sadao Tsuboi、Tsutomu Inokuchi

  DOI：10.1016/j.tet.2008.08.051

  日期：2008.11

  A new TEMPO-mediated catalytic oxidation method in combination with Py center dot HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3 center dot Poly(4-vinylpyridine) HBr3 can be used in place of Py center dot HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols Such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry. (C) 2008 Elsevier Ltd. All rights reserved.
• Direct electroreduction or use of an electrogenerated base : two ways for the coupling of polyhalogenated compounds with aldehydes or ketones.
  作者：Rachid Barhdadi、Blandine Simsen、Michel Troupel、Jean-Yves Nédélec

  DOI：10.1016/s0040-4020(96)01073-3

  日期：1997.2

  The electrochemical coupling of polyhalogenated compounds with carbonyl compounds is achieved in two ways. A carbanion RX(n)(-) is generated either by the direct electroreduction of RX(n)Cl or by deprotonation of RX(n)H. In this latter case the base Ph(-) is electrogenerated by reduction of iodobenzene. All electrolysis were carried out in an undivided cell fitted with a cadmium-coated cathode and an aluminium or magnesium sacrificial anode. (C) 1997, Elsevier Science Ltd.