4-叔-丁基-2,6-二(1-羟基-1-(三氟甲基)-2,2,2-三氟乙基)碘苯 | 101697-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-叔-丁基-2,6-二(1-羟基-1-(三氟甲基)-2,2,2-三氟乙基)碘苯
• 英文名称: 4-tert-butyl-2,6-bis<1-hydroxy-1-(trifluoromethyl)-2,2,2-trifluoroethyl>iodobenzene
• 英文别名: 4-tert-Butyl-2,6-bis(1-hydroxy-1-(trifluoromethyl)-2,2,2-trifluoroethyl)iodobenzene；2-[5-tert-butyl-3-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-iodophenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol
• CAS: 101697-28-3
• 化学式: C₁₆H₁₃F₁₂IO₂
• 分子量: 592.163
• InChiKey: OQSMDYOVGMLBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-叔-丁基-2,6-二(1-羟基-1-(三氟甲基)-2,2,2-三氟乙基)碘苯 在 fluorine 作用下， 反应 0.25h， 以100%的产率得到1,1-difluoro-10-tert-butyl-3,3,7,7-tetrakis(trifluoromethyl)-4,6-benzo-1-ioda-2,8-dioxabicyclo<3.3.0>octane
  参考文献：
  名称：

  An organic tridentate ligand stabilizing a 10-I-4 iodinane oxide and related species

  摘要：

  The tridentate ligand of iodinane 7, with electronegative apical oxygens joined by five-membered rings to an electropositive equatorial carbon, strongly stabilizes pseudo-trigonal-bipyramidal (PSI-TBP) 10-I-3 species 7, as well as 10-I-4 species such as iodinane oxide 5. Fluorination of 7 forms a pseudooctahedral (PSI-Oc) 12-I-5 periodinane, 4, which is easily hydrolyzed to 5, or reacts with Lewis acids to form 10-I-4 fluoroperiodonium cation 8. The equatorial I+-O- bond of 5 reacts with electrophiles at the oxygen [with trifluoroacetyl triflate (TFAT) to give 10-I-4 (trifluoroacetoxy)periodonium triflate 12; with triflic acid (TfOH) to form the 10-I-4 hydroxyperiodonium triflate 9; and with trifluoroacetic anhydride (TFAA) to form the 12-I-5 bis(trifluoroacetoxy)periodinane 11]. Small amounts of tetrabutylammonium hydroxide give nucleophilic addition to the iodine of 5 to form 12-I-5 intermediates (18) leading to rapid inversion of geometry at the 10-I-4 center of the iodinane oxide. Excess KOH cleaves the C-I bond of 5, forming the reduced arenediol 17. Diphenyldialkoxysulfurane 14 converts 5 to dialkoxyperiodinane 13, forming diphenyl sulfoxide. Iodine oxide 5 is a strong oxidizing agent, rapidly oxidizing HCl to Cl2, or pinacol to acetone. Oxidation of a diaryl sulfide to the sulfoxide and the sulfone occurs unselectively, but slowly, at 160-degrees-C with pure 5. With a catalytic amount of TFAA, selective oxidation of the diaryl sulfide to the sulfoxide by 5 is rapid at room temperature.

  DOI：

  10.1021/jo00023a022
• 作为产物：
  描述：

  1,4-dihydro-8-bromo-6-tert-butyl-2,2-dimethyl-4,4-bis(trifluoromethyl)-2H-<3,1>benzoxazine 在 正丁基锂 、 硫酸 、 氢气 、 亚硝酸 、 尿素 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 4-叔-丁基-2,6-二(1-羟基-1-(三氟甲基)-2,2,2-三氟乙基)碘苯
  参考文献：
  名称：

  A stable aryldialkoxybrominane. Synthesis, structure, and reactions of an organo-nonmetallic 10-Br-3 species

  摘要：

  DOI：

  10.1021/ja00273a041

文献信息

• NGUYEN T. T.; WILSON S. R.; MARTIN J. C., J. AMER. CHEM. SOC., 108,(1986) N 13, 3804-3811
  作者：NGUYEN T. T.、 WILSON S. R.、 MARTIN J. C.

  DOI：——

  日期：——
• A stable aryldialkoxybrominane. Synthesis, structure, and reactions of an organo-nonmetallic 10-Br-3 species
  作者：T. T. Nguyen、S. R. Wilson、J. C. Martin

  DOI：10.1021/ja00273a041

  日期：1986.6
• An organic tridentate ligand stabilizing a 10-I-4 iodinane oxide and related species
  作者：L. Weclas-Henderson、T. T. Nguyen、R. A. Hayes、J. C. Martin

  DOI：10.1021/jo00023a022

  日期：1991.11

  The tridentate ligand of iodinane 7, with electronegative apical oxygens joined by five-membered rings to an electropositive equatorial carbon, strongly stabilizes pseudo-trigonal-bipyramidal (PSI-TBP) 10-I-3 species 7, as well as 10-I-4 species such as iodinane oxide 5. Fluorination of 7 forms a pseudooctahedral (PSI-Oc) 12-I-5 periodinane, 4, which is easily hydrolyzed to 5, or reacts with Lewis acids to form 10-I-4 fluoroperiodonium cation 8. The equatorial I+-O- bond of 5 reacts with electrophiles at the oxygen [with trifluoroacetyl triflate (TFAT) to give 10-I-4 (trifluoroacetoxy)periodonium triflate 12; with triflic acid (TfOH) to form the 10-I-4 hydroxyperiodonium triflate 9; and with trifluoroacetic anhydride (TFAA) to form the 12-I-5 bis(trifluoroacetoxy)periodinane 11]. Small amounts of tetrabutylammonium hydroxide give nucleophilic addition to the iodine of 5 to form 12-I-5 intermediates (18) leading to rapid inversion of geometry at the 10-I-4 center of the iodinane oxide. Excess KOH cleaves the C-I bond of 5, forming the reduced arenediol 17. Diphenyldialkoxysulfurane 14 converts 5 to dialkoxyperiodinane 13, forming diphenyl sulfoxide. Iodine oxide 5 is a strong oxidizing agent, rapidly oxidizing HCl to Cl2, or pinacol to acetone. Oxidation of a diaryl sulfide to the sulfoxide and the sulfone occurs unselectively, but slowly, at 160-degrees-C with pure 5. With a catalytic amount of TFAA, selective oxidation of the diaryl sulfide to the sulfoxide by 5 is rapid at room temperature.