3,3'-bis-(trifluoromethyl)thiobenzophenone | 172222-69-4

• 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: 3,3'-bis-(trifluoromethyl)thiobenzophenone
• 英文别名: Bis[3-(trifluoromethyl)phenyl]methanethione；bis[3-(trifluoromethyl)phenyl]methanethione
• CAS: 172222-69-4
• 化学式: C₁₅H₈F₆S
• 分子量: 334.285
• InChiKey: XXZRZWBZVVTAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3'-bis-(trifluoromethyl)thiobenzophenone 在 三氟甲磺酸 、 双氧水 、 甲基三氧化铼(VII) 作用下， 以 水 、 乙腈 为溶剂， 以92%的产率得到3,3'-bis(trifluoromethyl)thiobenzophenone S-oxide
  参考文献：
  名称：

  A Convenient Preparation of Sulfines (R₂CSO) from Thioketones

  摘要：

  DOI：

  10.1021/jo990967p
• 作为产物：
  描述：

  3,3'-双(三氟甲基)苯甲酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 3,3'-bis-(trifluoromethyl)thiobenzophenone
  参考文献：
  名称：

  通过Thia-Paternò-Büchi引发的多米诺光化学反应形成四氢噻吩

  摘要：

  我们已经建立了从硫代二苯甲酮衍生物和丙烯腈到硫杂环丁烷或四氢噻吩化合物的光化学途径，其中产物的选择性通过简单调整溶液中试剂的浓度来控制。通过thia-Paternò-Büchi反应，然后以多米诺法或逐步方式进行先前未知的区域选择性光化学环扩大反应，制备了五元环含硫化合物的小型文库。提出了通过由光激发的硫代羰基化合物提供的卡宾物质使该环扩大反应合理化的机理。

  DOI：

  10.1021/acs.orglett.0c03128

文献信息

• Stereochemistry of the [4 + 2] Cycloaddition of Diarylselenoketones with Conjugated Dienes
  作者：Stefanie Wilker、Gerhard Erker

  DOI：10.1021/ja00149a015

  日期：1995.11

  The ylides Ph(3)P=(CArAr2)-Ar-1 1a-g (Ar C6H5, p-C6H4Cl p-C6H4F, m-C6H4CF3, P-C(6)H4OCH(3), p-C6H4CH3) were treated with elemental selenium (similar to 80 degrees C) to give the corresponding selenoketones Se=CAr(1)Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis, trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admired with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cydoaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic ''leakage'' to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.