84392-17-6 Usage
Chemical Properties
White solid
Originator
Xenalipin ,Wellcome (GSK)
Uses
4''-(Trifluoromethyl)-2-biphenylcarboxylic Acid, is a novel compound which has been found to be effective hypolipidemic agent in animal species. It is also an intermediate in the synthesis of various pharmaceutical compounds, such as Cannabinol (C175350).
Manufacturing Process
a). Preparation of 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-trifluoromethylbiphenyl:
A mechanically stirred solution of magnesium turnings (5.1 g, 0.21 mole)
Mallinckrodt, for Grignards reaction, and 2-(2-methoxyphenyl)-4,4-dimethyl-
2-oxazoline (41 g, 0.2 mole) in 50 mL dry tetrahydrofuran under nitrogen was
prepared. To this was added a crystal of iodine, 1 mL of dibromethane and 2
mL of neat p-bromotrifluoromethylbenzene to initiate the Grignard reaction.
Following initiation of the reaction, the remainder of the p-
bromotrifluoromethylbenzene (50 g, 0.22 mole total) in 100mL dry
tetrahydrofuran was added dropwise at a rate sufficient to maintain the
reaction at gentle reflux. The addition took 1 hour. At the end of the addition
period, the reaction mixture was heated to reflux for 3 hours. The reaction
mixture was then cooled to room temperature and 10 mL water was added
dropwise to coagulate the salts. The tetrahydrofuran was decanted and the
remaining solids were slurried twice with 300 mL ethyl ether and twice with
300 mL dichloromethane. Each organic extract was decanted from the solids
in turn and combined and evaporated under reduced pressure to an oil.
This oil was redissolved in 300 mL dichloromethane, washed once with 100
mL water and once with 10 mL saturated sodium chloride solution, dried and
concentrated under reduced pressure. The resulting residue was distilled
under reduced pressure (0.040 mm, 95.degree.) to yield 2-(4,4-dimethyl-2-
oxazoline-2-yl)-4'-trifluoromethylbiphenyl, yield 33%. A sample was
recrystallized from 30-60°C petroleum ether (melting point 50-51°C).
b). Preparation of 4'-(trifluoromethyl)-2-biphenylcarboxylic acid:
A solution of 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-trifluoromethylbiphenyl (3.5
g, 0.011 mole) in 60 mL 6 N hydrochloric acid was stirred at vigorous reflux
for 2 hr. The reaction mixture was then cooled to room temperature and
extracted with methylene chloride. The organic extracts were dried and
concentrated under reduced pressure to yield a solid. Recrystallisation from
ethyl ether/pentane afforded 4'-(trifluoromethyl)-2-biphenyl carboxylic acid,
yield 86% (melting point 167-169°C).
Therapeutic Function
Antihyperlipidemic
General Description
4′-(Trifluoromethyl)-2-biphenylcarboxylic acid (xenalipin) has been tested as an effective hypolipidemic agent in animal species. It has been shown to cause significant reduction in serum cholesterol and triglyceride levels in animal models and would be beneficial in therapy for hyperlipidemia. Synthesis of 4′-(trifluoromethyl)-2-biphenylcarboxylic acid (xenalipin) has been reported. Xenalipin has been synthesized in the [14C]-labelled form, with specific activity 21.0mCi/mmol, which is suitable for the metabolism and distribution studies in animals.
Check Digit Verification of cas no
The CAS Registry Mumber 84392-17-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,4,3,9 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 84392-17:
(7*8)+(6*4)+(5*3)+(4*9)+(3*2)+(2*1)+(1*7)=146
146 % 10 = 6
So 84392-17-6 is a valid CAS Registry Number.
84392-17-6Relevant articles and documents
Stepwise benzylic oxygenation via uranyl-photocatalysis
Hu, Deqing,Jiang, Xuefeng
supporting information, p. 124 - 129 (2022/01/19)
Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.
Palladium-catalyzed intramolecular aromatic C-H acylation of 2-arylbenzoyl fluorides
Hayakawa, Kazuki,Ikai, Kana,Ogiwara, Yohei,Sakai, Norio,Sakurai, Yuka
, p. 1882 - 1893 (2021/08/13)
The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)2/PCy3 system is described. A wide range of 2-arylbenzoyl fluoride derivatives can be used as fluorenone precursors and the reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds. The reaction can be applied to the synthesis of indenofluorenedione derivatives and to the construction of other molecules with fivemembered rings.
Visible-Light-Induced Arene C(sp 2)-H Lactonization Promoted by DDQ and tert -Butyl Nitrite
Chen, Bajin,Hu, Baoxiang,Hu, Xinquan,Jin, Liqun,Li, Meichao,Shen, Zhenlu,Sun, Nan,Wang, Shengpeng,Wang, Yiqing
supporting information, p. 261 - 266 (2020/02/18)
A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp 2)-H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert -butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.
