2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol | 85914-80-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol
• CAS: 85914-80-3
• 化学式: C₁₆H₁₄F₄O₂
• 分子量: 314.28
• InChiKey: OYZDMPBNMZWFTM-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(Solv: hexane (110-54-3))
• 沸点：
  472.6±45.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol 在 Oxone 、 potassium 2-iodo-5-methylbenzenesulfonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以71%的产率得到2,2,3,3-四氟-1,4-二苯基丁烷-1,4-二酮
  参考文献：
  名称：

  氟代烷基取代的甲醇衍生物氧化的新条目：有机碘（V）试剂催化氧化的范围和限制

  摘要：

  钠2-碘和过硫酸氢钾的催化量的影响下的各种氟烷基取代甲醇衍生物的氧化®在CH 3 CN或CH 3 NO 2详细进行了研究。通过与其他氧化方法（如Dess-Martin，PDC和Swern氧化方法）进行比较，还评估了新开发的氧化方法的效率。

  DOI：

  10.1016/j.jfluchem.2012.03.002
• 作为产物：
  描述：

  2,2,3,3-四氟-1,4-二苯基丁烷-1,4-二酮 在 bromomagnesium ethoxide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol
  参考文献：
  名称：

  Dormidontov, Yu. P.; Shadrina, L. P., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 241 - 244

  摘要：

  DOI：

文献信息

• 1,2-Bis(dimethylphenylsilyl)tetrafluoroethane. Application to the Trifluorovinylation and Tetrafluoroethylenation of Carbonyl Compounds
  作者：Toshiki Hagiwara、Takamasa Fuchikami

  DOI：10.1246/cl.1997.787

  日期：1997.8

  The reaction of 1,2-bis(dimethylphenylsilyl)tetrafluoroethane with a small excess of benzaldehyde in the presence of the promoter gave the trifluorovinylated product, 1,1,2-trifluoro-3-phenylpropen-3-ol, selectively. The tetrafluoroethylenated product, 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol, was also obtained in benzaldehyde solvent or at low temperatures.

  在促进剂存在的情况下，1,2-双（二甲基苯基硅基）四氟乙烷与少量过量的苯甲醛反应，可选择性地得到三氟乙烯基化产物--1,1,2-三氟-3-苯基丙烯-3-醇。在苯甲醛溶剂中或低温条件下，也能得到四氟乙烯化产物 2,2,3,3-四氟-1,4-二苯基丁烷-1,4-二醇。
• Preparation of and Fluoroalkylation with (Chlorodifluoromethyl)trimethylsilane, Difluorobis(trimethylsilyl)methane, and 1,1,2,2-Tetrafluoro-1,2-bis(trimethylsilyl)ethane
  作者：Andrei K. Yudin、G. K. Surya Prakash、Denis Deffieux、Michael Bradley、Robert Bau、George A. Olah

  DOI：10.1021/ja962990n

  日期：1997.2.1

  CF2BrCl reacts with aluminum/N-methylpyrrolidinone in the presence of chlorotrimethylsilane to give Me(3)SiCF(2)Cl in high yield. Similarly, CF2Br2 gives Me(3)SiCF(2)Br with bromotrimethylsilane. Chlorodifluoromethylation of aldehydes using Me(3)SiCF(2)Cl and a catalytic amount of TBAF in polar solvents occurs at room temperature, providing difluoromethylated alcohols in two steps. Electroreduction of Me(3)SiCF(2)Cl in the presence of chlorotrimethylsilane gives Me(3)SiCF(2)SiMe(3) (anion-derived product) and Me(3)SiCF(2)CF(2)SiMe(3) (radical-derived product). Using THF/HMPA strongly favors the former, whereas THF/TDA-1 (tris(3,6-dioxaheptyl)amine) the latter. Me(3)SiCF(2)-SiMe(3) difluoromethylates aldehydes acting as a difluoromethylene dianion (''CF22-'' equivalent), whereas Me(3)SiCF(2)-CF(2)SiMe(3) acts at room temperature as an in situ source for the perfluorovinyl anion (due to beta-elimination of fluorotrimethylsilane). However, at low temperature the elimination pathway is suppressed and tetrafluoroethylene dianion (''-CF2CF2-'' equivalent) behavior is observed, The structure of Me(3)SiCF(2)CF(2)SiMe(3) was analyzed by X-ray diffraction. All of the studied fluoroalkylating reagents are moisture- and air-stable and can be readily obtained from a single convenient precursor (CF2BrCl).
• DORMIDONTOV, YU. P.;SHADRINA, L. P., ZH. ORGAN. XIMII, 1983, 19, N 2, 269-273
  作者：DORMIDONTOV, YU. P.、SHADRINA, L. P.

  DOI：——

  日期：——
• A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation
  作者：Yusuke Tanaka、Takashi Ishihara、Tsutomu Konno

  DOI：10.1016/j.jfluchem.2012.03.002

  日期：2012.5

  Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone® in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess–Martin, PDC, and Swern oxidation.

  钠2-碘和过硫酸氢钾的催化量的影响下的各种氟烷基取代甲醇衍生物的氧化®在CH 3 CN或CH 3 NO 2详细进行了研究。通过与其他氧化方法（如Dess-Martin，PDC和Swern氧化方法）进行比较，还评估了新开发的氧化方法的效率。
• Dormidontov, Yu. P.; Shadrina, L. P., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 241 - 244
  作者：Dormidontov, Yu. P.、Shadrina, L. P.

  DOI：——

  日期：——