3.4- Methylenedioxy-6- phenol

CHjNaO 124-41-4) see Atorvastatin calcium Brinzolamide Ciprofloxacin Cisapride Dextrothyroxine Epirizole Hydroxyprogesterone Metaclazepam Moxifloxacin hydrochloride Moxonidine Oxcarbazepine Pantoprazole sodium Sulfadimethoxine Sulfalene Sulfamcthoxypyridazine Tacrolimus Vincamine sodium 3,4-(methylenedioxy)phenolate (CjHjNaOj 57f74-0i-5) sec Paroxetine sodium 4-nitrophenolate... 

A very interesting and promising synthesis of pterocarpans (76CC500) involves Heck arylation of a 2-chromene (Scheme 53). The requisite chloromercuriphenol is readily available through the action of mercury(II) acetate, followed by sodium chloride, on 3,4-(methylenedioxy)phenol. 

PdClg added to a rapidly stirred soln. of 2-(tran -l-propenyl)-4,5-methylenedioxy-phenol and Na-acetate in methanol-water, stirring continued 2 hrs. at ca. 38°, then allowed to stand 1 hr. at room temp. carpanone. Y 46%. - Five contiguous asym. centers with the desired stereochemistry are introduced in a single step by this net two-electron oxidation. O. L. Chapman et al., Am. Soc. 93, 6696 (1971). 

Obtained by reaction of methoxyacetonitrile with 3-methoxy-4,5-(methylenedioxy)phenol (Hoesch reaction) [4905], (41%) [4920], (29%) [4904]. 

Catechols can be protected as diethers or diesters by methods that have been described to protect phenols. However, formation of cyclic acetals and ketals (e.g., methylenedioxy, acetonide, cyclohexylidenedioxy, diphenylmethylenedioxy derivatives) or cyclic esters (e.g., borates or carbonates) selectively protects the two adjacent hydroxyl groups in the presence of isolated phenol groups. 

Corypalline, CnHijOjN (Corydalis spp. Nos. 9, 22 list, p. 170). This phenolic base, m.p. 168°, picrate, m.p. 178°, contains one methoxyl group and on methylation yields 2-methyl-6 7-dimethoxytetrahydrof5oquinoline, Ci2Hi,02N, m.p. 82°, and on ethylation, 2-methyl-6-methoxy-7-ethoxy-tetrahydrofsoquinoline, m.p. 65°, whence the free hydroxyl appears to be at C and this has been confirmed by the synthesis of corypalline by a method analogous with that used by Spath, Orekhov and Kuffner. Corypalline is therefore hydrohydrastinine (XII) with the methylenedioxy group replaced by MeO at C and. OH at C (Manske). ... 

Phenylpropanes are aromatic compounds with a propyl side chain attached to the benzene ring, which can be derived directly from phenylalanine. Naturally occurring phenylpropanoids often contain oxygenated substituents, e.g. OH, OMe or methylenedioxy, on the benzene ring. Phenylpropanoids with hydroxyl substituent(s) on the benzene ring belongs to the group of phenolics, e.g. caffeic acid and coumaric acid. 

Bivalent radicals of the form O—Y—O are named by adding -dioxy to the name of the bivalent radicals except when forming part of a ring system. Examples are —O— CH2—O — (methylenedioxy), —O—CO — O— (carbonyldioxy), and —O — S02 — O— (sulfonyldioxy). Anions derived from alcohols or phenols are named by changing the final -ol to -olate. 

Photolytic cyclization of the phenolic bromo compounds 278 and 279 led to ( + )-oxocrinine (275) (methylenedioxy instead of methoxy-hydroxy) and ( )-oxomaritidine (275), known intermediates to crinine and maritidine (277) (59, 60). Oxocrinine was also obtained by photolysis of the isomeric bromophenol 280 (61). 

The aryl group substitution patterns found in lignans are delineated in Scheme 2. The rings may be mono-, di-, tri-, or tetrasubstituted by the common phenolic hydroxyl, methyl ether and methylenedioxy groups. With a few exceptions (isolated notably from mammalian sources), all lignans have an oxygenated substituent para... 

Mecambroline was isolated from Meconopsis carnbrica Vig. (Papaver-aceae), and the elemental data indicated the value C18H17O3N. The alkaloid melts at 145°, and exhibits [aj +76° (in CHCI3). A hydrochloride salt was obtained (inp 264°-266°) as well as a picrate (mp 179°-180°). Color tests showed the presence of a methylenedioxy and a phenolic group. The UV-spectrum had 308 and 275 mp, (log e 4.0 and 4.2), with a shoulder at 269 mp (log e 4.1), typical of a 1,2,10-tri-substituted aporphine. 0-Methylation with diazomethane gave a base (mp 111°-112°) 6). 

The location of the phenolic hydroxyl at C-10 and the placement of the methylenedioxy group in ring A became possible when it was found that hydrogenation of deoxythalidastine afforded tetrahydrothalifendine (XXXV R = H). 

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