S-(Perfluorooctyl)dibenzothiophenium triflate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: S-(Perfluorooctyl)dibenzothiophenium triflate
• 英文别名: S-(perfluoro-n-octyl)dibenzothiophenium triflate；5-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctyl)dibenzothiophen-5-ium;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₂₀H₈F₁₇S
• 分子量: 752.393
• InChiKey: JHKYMHIBBPKDHR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  S-(Perfluorooctyl)dibenzothiophenium triflate 在 硫酸 作用下， 以85%的产率得到S-(Perfluoro-n-octyl)dibenzothiophenium-3-sulfonate
  参考文献：
  名称：

  Useful electrophilic trifluoromethylating agents; S-, Se- and Te-(trifluoromethyl)dibenzo-thio-, -seleno- and -telluro-phenium-3-sulfonates

  摘要：

  Se, Se- and Te-(Trifluoromethyl) dibenzo-thio-, -seleno- and -telluro-phenium-3-sulfonates and their dimethyl and nitro derivatives have been synthesized in good yield by sulfonation of the corresponding (trifluoromethyl)dibenzocyclic chalcogen salts with fuming sulfuric acid or by sulfonation followed by nitration. The practical use of these power-variable trifluoromethylating agents has been demonstrated. Thus, they provide good yields of trifluoromethylated products, and the by-product (a salt of dibenzothiophene-3-sulfonic acid or an analog) was easily removed from the products by filtration or by washing with water. S-(Perfluoro-ethyl, -n-butyl- and -n-octyl)dibenzothiophenium-3-sulfonates have also been synthesized and a similar perfluoroalkylation using one of them has been accomplished.

  DOI：

  10.1016/0022-1139(95)03253-a
• 作为产物：
  描述：

  全氟辛基碘烷 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 122.0h， 生成 S-(Perfluorooctyl)dibenzothiophenium triflate
  参考文献：
  名称：

  功率可变的亲电三氟甲基化剂。S-、Se-和Te-(三氟甲基)二苯并硫代-、-硒-和-碲鎓盐系统

  摘要：

  S-、Se-和 Te-三氟甲基化二苯并杂环鎓盐、它们的衍生物和相关盐是通过 2-[（三氟甲基）硫代或硒代]联苯和三氟甲磺酸 (TfOH) 或 HBF 的混合物的直接氟化合成的4 醚化物，通过使用 Tf 2 O 和 (CH 3 ) 2 SO 对 2-[(三氟甲基) 碲] 联苯进行新型碲活化，或通过鎓的衍生，用 Tf 2 O 处理相应的亚砜和硒氧化物得到的盐。反应性检查表明，与非杂环盐相比，三氟甲基杂环盐具有很强的反应性，并表明该杂环盐体系可作为广泛适用的三氟甲基化剂的来源

  DOI：

  10.1021/ja00059a009

文献信息

• Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-<i>ortho</i>-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines
  作者：Dong Liang、Li-Ping Tan、Wen-Jing Xiao、Jia-Rong Chen

  DOI：10.1039/d0cc00747a

  日期：——

  A [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with formaldimines derived from 1,3,5-triazinanes is described.

  描述了光发生的aza-ortho-醌甲烷与从1,3,5-三嗪烷衍生的甲醛二胺进行的[4+2]环加成反应。
• Perfluoroalkyl-containing compound
  申请人：Sagami Chemical Research Center

  公开号：US05066795A1

  公开（公告）日：1991-11-19

  A (perfluoroalkyl)dibenzonium salt represented by the following general formula ##STR1## wherein R.sub.f represents a perfluoroalkyl group having 1 to 10 carbon atoms, A represents a sulfur of selenium atom, R.sup.1 and R.sup.2, independently from each other, represent a hydrogen atom or a nitro group, X.sup..crclbar. represents a conjugated base of Bronsted acid, and n is 0 or 1. The said compound is useful as a reagent for introducing a perfluoroalkyl group.

  以下是翻译结果： 一种由下列一般式表示的(perfluoroalkyl)dibenzonium盐：##STR1## 其中R.sub.f表示具有1至10个碳原子的全氟烷基，A表示硫或硒原子，R.sup.1和R.sup.2独立地表示氢原子或硝基，X.sup..crclbar.表示Bronsted酸的共轭碱，n为0或1。该化合物可用作引入全氟烷基的试剂。
• New Method for Trifluoromethylation of Enolate Anions and Applications to Regio-, Diastereo- and Enantioselective Trifluoromethylation
  作者：Teruo Umemoto、Kenji Adachi

  DOI：10.1021/jo00098a030

  日期：1994.9

  Assessment was made of the effectiveness of different boron Lewis acids in mediating the trifluoromethylation of reactive enolate anions with S- and Se-(trifluoromethyl)chalcogen salts. Treatment of potassium or lithium enolates derived in situ from carbonyl compounds or enol trimethylsilyl ethers with S-(trifluoromethyl)dibenzothiophenium triflate (1) in the presence of 2-phenyl-1,3,2-benzodioxaborole (4) produced trifluoromethylated carbonyl compounds in high yields. Iq this manner, various alpha-CF3 ketones, gamma-CF3-alpha,beta-unsaturated ketones, and an alpha-CF3 ester were synthesized. Perfluorooctylation was similarly conducted using S-(perfluorooctyl)dibenzothiophenium triflate and 4. Thus, a balance of the reactivity of the reactants was essential for these electrophilic perfluoroalkylations. The deprotonation of 2-methylcyclohexanone with KN(SiMe(3))(2) followed by trifluoromethylation gave the 6-trifluoromethylated product regioselectively. In the trifluoromethylation of potassium enolate 16 of 4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone, the use of bulky 2-mesitylphenanthro[9,10-d]-1,3,2-dioxaborole (15) led to the diastereo-selective formation of the thermodynamically less stable CF3-isomer 17 beta. For enantioselective trifluoromethylation, optically active (S)-4-phenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin(19) and its 3,3'-diphenyl derivative 20 were synthesized. The trifluoromethylation of the potassium enolate of propiophenone with 1 in the presence of 20 afforded optically active alpha-CF3-propiophenone in 45% ee yield. Thus, a new and versatile method for selective trifluoromethylation has been developed.
• (HALOALKYL)DIBENZO-ONIUM SULFONATE, PROCESS FOR PRODUCING THE SAME, AND HALOALKYLATING AGENT AND METHOD
  申请人：DAIKIN INDUSTRIES, LIMITED

  公开号：EP0647638B1

  公开（公告）日：1998-10-07
• US5066795A
  申请人：——

  公开号：US5066795A

  公开（公告）日：1991-11-19