2-Methyl-2-trifluoromethyl-1,3-cyclopentanedione | 129922-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-2-trifluoromethyl-1,3-cyclopentanedione
• 英文别名: 2-methyl-2-(trifluoromethyl)-1,3-cyclopentadione；2-Methyl-2-(trifluoromethyl)-1,3-cyclopentanedione；2-methyl-2-(trifluoromethyl)cyclopentane-1,3-dione
• CAS: 129922-40-3
• 化学式: C₇H₇F₃O₂
• 分子量: 180.127
• InChiKey: RGTFODAPUZVSKG-UHFFFAOYSA-N

物化性质

• 沸点：
  202.0±40.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-环戊二酮 、 S-(三氟甲基)二苯并噻吩-3-磺酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到2-Methyl-2-trifluoromethyl-1,3-cyclopentanedione
  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

文献信息

• Power-variable electrophilic trifluoromethylating agents. S-, Se-, and Te-(trifluoromethyl)dibenzothio-, -seleno-, and -tellurophenium salt system
  作者：Teruo Umemoto、Sumi Ishihara

  DOI：10.1021/ja00059a009

  日期：1993.3

  Te-trifluoromethylated dibenzoheterocyclic onium salts, their derivatives, and related salts were synthesized by the direct fluorination of a mixture of 2-[(trifluoromethyl)thio- or seleno]biphenyls and triflic acid (TfOH) or HBF 4 etherate, by treatment of the corresponding sulfoxides and selenoxides with Tf 2 O by a new type of tellurium activation of 2-[(trifluoromethyl)telluro]biphenyls with Tf 2 O and (CH

  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
• Synthesis and applications of S-(trifluoromethyl)-2,8-bis(trifluoromethoxy)dibenzothiophenium triflate (Umemoto reagent IV)
  作者：Sagar R. Mudshinge、Gerald B. Hammond、Teruo Umemoto

  DOI：10.1016/j.jfluchem.2022.110015

  日期：2022.9

  trifluoromethylating agent, S-(trifluoromethyl)-2,8-bis(trifluoromethoxy)dibenzothiophenium triflate (Umemoto reagent IV), was developed. Due to the extraordinary electronic effect of trifluoromethoxy group, Umemoto reagent IV was easily synthesized by a one-pot method from readily available 3,3’-bis(trifluoromethoxy)biphenyl. It was shown that Umemoto reagent IV was more powerful than Umemoto reagent II and could trifluoromethylate

  开发了一种新型、强效且易于操作的亲电三氟甲基化试剂，S- (三氟甲基)-2,8-双(三氟甲氧基)二苯并噻吩鎓三氟甲磺酸盐（Umemoto试剂IV）。由于三氟甲氧基的非凡电子效应，Umemoto试剂IV可以通过易得的3,3'-双(三氟甲氧基)联苯通过一锅法轻松合成。结果表明，Umemoto 试剂 IV 比 Umemoto 试剂 II 更强大，可以更有效地对多种亲核底物进行三氟甲基化。此外，Umemoto试剂IV成功地用于制备有用的三氟甲氧基化剂三氟甲基九氟磺酸酯。实现了用三氟甲磺酸酐将 2,8-双（三氟甲氧基）二苯并噻吩直接转化为 Umemoto 试剂 IV，尽管产率较低。
• Hydrophobic compounds for optically active devices
  申请人：Merck Patent GmbH

  公开号：US11014901B2

  公开（公告）日：2021-05-25

  The present invention relates to novel compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic devices comprising such compounds.

  本发明涉及新型化合物，特别是包含光活性单元的化合物，所述新型化合物特别适用于组合物和眼科设备，以及包含此类化合物的组合物和眼科设备。
• Power-variable trifluoromethylating agents, (trifluoromethyl)dibenzothio- and -selenophenium salt system
  作者：Umemoto Teruo、Ishihara Sumi

  DOI：10.1016/s0040-4039(00)94447-2

  日期：1990.1
• (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