1-phenyl-2-phenylthio-1-trifluoroacetoxyethane | 98289-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-phenylthio-1-trifluoroacetoxyethane
• 英文别名: (1-phenyl-2-phenylsulfanylethyl) 2,2,2-trifluoroacetate
• CAS: 98289-60-2
• 化学式: C₁₆H₁₃F₃O₂S
• 分子量: 326.339
• InChiKey: QOILVFUHOFDLSO-UHFFFAOYSA-N

物化性质

• 沸点：
  389.0±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-phenylthio-1-trifluoroacetoxyethane 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 生成 1-phenyl-2-phenylsulfanyl-ethanol
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o
• 作为产物：
  描述：

  苯乙烯 、 phenylsulfenyl trifluoroacetate 生成 1-phenyl-2-phenylthio-1-trifluoroacetoxyethane
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o

文献信息

• Additions to alkenes via metal ion-promoted oxidation of dialkyl and diaryl disulphides
  作者：Alan Bewick、John M. Mellor、W. Martin Owton

  DOI：10.1039/p19850001039

  日期：——

  Reactions of alkenes with di-n-propyl, diphenyl, and dibenzyl disulphide in the presence of lead(IV) salts in trifluoroacetic acid-dichloromethane are described. The products, vicinal trifluoroacetoxy-sulphides, are obtained in higher yields with manganese (III) salts as the oxidant. Alternative reaction conditions with use of iron(III) salts or in the absence of added metal salts are also described

  描述了在三氟乙酸-二氯甲烷中铅（IV）盐存在下烯烃与二正丙基，二苯基和二苄基二硫化物的反应。用锰（III）盐作为氧化剂，可以以较高的产率获得邻位的三氟乙酰氧基-硫化物。使用铁的替代反应条件（III还描述了）盐或不存在添加的金属盐的情况。在Ritter条件下，衍生自二苯基二硫化物的三氟乙酰氧基硫化物与乙腈反应，生成乙酰胺基硫化物，但是衍生自苄基乙酰胺的另一种反应途径，衍生自二苄基二硫化物的三氟乙酰氧基硫化物仅以较差的产率得到邻位乙酰酰胺基硫化物。描述了乙酰氨基硫化物到氨基硫化物和乙酰氨基硫醇的转化。
• BEWICK, A.;MELLOR, J. M.;OWTON, W. M., J. CHEM. SOC. PERKIN TRANS., 1985, N 5, 1039-1044
  作者：BEWICK, A.、MELLOR, J. M.、OWTON, W. M.

  DOI：——

  日期：——