4,4′-Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate

Dimethyl biphenyl-4,4'-dicarboxylate (Biphenyl dimethyl dicarboxylate) is a hepatoprotectant obtained from Schizandra fructus and may induce a signal transduction similar to that associated with IFN[1].

Nissel has been investigated for the treatment of Chronic Liver Disease.

Reaction flask (10 mL) equipped with stirring bar was charged with (4-(methoxycarbonyl)phenylboronic acid (66 mg, 0.91 mmol), ethanol (96%) (2 mL), [{Pd(mu-OH)Cl(IPr)}2] (5 10-4 g, 4.55 × 10-7 mol). Reaction mixture was stirred at 22 C for 6 h. Aftercompletion of the reaction solvent was evaporated, the residue was dissolved in hexane (5 mL) andextracted with water (2 × 2 mL). The organic layer was dried over magnesium sulphate, and hexanewas evaporated under reduced pressure. 96 mg of dimethyl[1, 1'-biphenyl]-4, 4'-dicarboxylate wasobtained as a white solid. Yield = 97%. 1H NMR (403 MHz, CDCl3, ppm) delta: 8.13 (d, J = 8.7 Hz, 4H), 7.69 (d, J = 8.7 Hz, 4H), 3.95 (s, 6H); 13C NMR (101 MHz, CDCl3, ppm) delta: 166.79, 153.16, 144.34, 130.19, 129.68, 127.23, 124.20, 52.2. MS (EI) m/z (%) = 270 (M+, 48), 255 (11), 239 (100), 211 (9), 209 (8), 153 (10), 152 (11), 59 (10).General procedure: 4.3. Catalytic tests: general procedure I for the Cu2(ophen)2catalyzed homocoupling for Table 2 A solution of the corresponding arylboronic acids (1.0 mmol), Cu2(ophen)2 (1.3 mg, 0.5 mol %), DMF (1.0 mL) in 5 mL round-bottomed ask was stirred under air and the reaction was moni-tored by TLC. After the substrate was consumed, the reaction con-versions were determined bygas chromatography (GC) analysis (FIDfrom AGILENT 7820) using a cross-linked (95%)-dimethyl-(5%)-diphenylpolysil-oxane column (HP-5, 30 m0.32 mm0.25 mm), helium, injector temperature 250 C, detector temperature 300 C, and oven temperature program 45 C (3 min)e20C/mine280 C(2 min). The resulting mixture was poured into brine (10 mL), andextracted with diethyl ether (310 mL). The organic layer waswashed with brine, dried over Mg2SO4, the residue was chromato-graphed via a short column of silica gel (petroleum ether: diethylether15:1) and evaporated under reduced pressure. The productswas determined by 1H NMR spectroscopy. All 1H NMR spectra weremeasured in CDCl3 with TMS as the internal standard.[0266] Allyl acetate (10 mmol) and aryl chloride (5 mmol) are introduced into a pyridine acetonitrile solution (AN=20 ml/Py=2 ml) that contains manganese dust (50 mmol), cobalt bromide dust (2 mmol), and ferrous bromide dust (5 mmol). The reaction mixture is brought to 50 C. and is stirred until aryl chloride completely disappears (not detectable in gas chromatography).

USED IN PREPN OF INSECT GROWTH REGULATORS

Molecular Weight:270.28
XLogP3:3.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:270.08920892
Monoisotopic Mass:270.08920892
Topological Polar Surface Area:52.6
Heavy Atom Count:20
Complexity:302
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes