Derivate des Methylendioxybenzols, 6. Mitt.: �ber die Gewinnung und elektrophile Substitutionen des Myristicins�uremethylesters und seiner Derivate

Dallacker, Franz; Gohlke, F.; Lipp, Maria

doi:10.1007/bf00899834

Cited by 6 publications

(10 citation statements)

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“…3-Methoxy-4,5-methylenedioxybenzaldehyde (Myristicin Aldehyde) (3d): 11 g, 61.06 mmol, 61% yield; off-white solid; mp 133-135 °C (lit. 39 132.5 °C); 1 H NMR (CDCl 3 , 500 MHz) δ 9.78 (1H, s, CHO), 7.26 (1H, s, H-Ph), 7.05 (1H, s, H-Ph), 6.12 (2H, s, OCH 2 O), 3.95 (3H, s, OCH 3 -3).…”

Section: Resultsmentioning

confidence: 99%

“…The precipitate was filtered, washed with 2 × 50 mL of ice water, and dried to afford 12a (0.85 g, 3.76 mmol, 88% yield) as an off-white solid: mp 174 °C (lit. 39 mp 175.5 °C).…”

Section: Resultsmentioning

confidence: 99%

“…The pH of the reaction mixture was adjusted to 3 with 18% HCl, and the resulting precipitate was collected, washed with ice water (2 × 50 mL), and dried to afford 12d (0.8 g, 4.07 mmol, 81.6% yield) as an off-white solid: mp 212 °C (lit. 39…”

Section: Resultsmentioning

confidence: 99%

“…This was further oxidized with KMnO 4 (6 g per 60 mL of H 2 O) in acetone (150 mL) at reflux for 4 h. Concentration of the residue followed by its recrystallization from EtOH afforded myristicin acid (12d) (4.5 g, 22.9 mmol, 7% yield; mp 212 °C; lit. 39 2,5-Dimethoxy-3,4-methylenedioxybenzyl Chloride. Neat SOCl 2 (47 mL, 644 mmol) was added dropwise to a stirred solution of 2,5dimethoxy-3,4-methylenedioxybenzyl alcohol 47 (66.5 g, 313 mmol) in dry benzene (150 mL) at 10 °C.…”

Section: Mp 211 °C)mentioning

confidence: 99%

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Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

et al. 2010

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Section: Resultsmentioning

confidence: 99%

“…The precipitate was filtered, washed with 2 × 50 mL of ice water, and dried to afford 12a (0.85 g, 3.76 mmol, 88% yield) as an off-white solid: mp 174 °C (lit. 39 mp 175.5 °C).…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Mp 211 °C)mentioning

confidence: 99%

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Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

et al. 2010

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“…The identity of the monoterpenes was obtained by comparing retention times of reference compounds whose characterization in parsley seed oil have been previously published (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23). The characterization of the phenol ether oxide was also obtained by retention times according to a previously published study (25).…”

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A Chemotaxonomic Evaluation ofPetroselinum crispum(Mill.) A. W. Hill (Parsley) Marketed in France

Lamarti

Badoc²,

Bouriquet

1991

Journal of Essential Oil Research

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Publication details, including instructions for authors and subscription information:ABSTRACT: Pentane extracts of the seeds (fruits) of 44 cultivars of parsley have been examined by gas chromatography. The curly-leaved parsley cultivars can be distinguished by their dark brown light mericarps which possess an essential oil rich in monoterpenes, particularlya-pinene (15.7-24.1%) andp-pinene (9.6-15.1%). Inrootparsley,onlya-pinene (10.6%), P-pinene (7.1%), myristicin (2.5%) and apiole (79.8%) were found, while apiole (30.4-67.5%) is the principal constituent of Giant Italian parsley. Myristicin (0.7-62.3%) was present in all parsley specimens analyzed.

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Derivate des Methylendioxybenzols, 39. Über Polyencarbonsäureimide des Methylendioxybenzols

Dallacker

Schubert

1975

Chem. Ber.

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Ein allgemein anwendbares Verfahren zur Dantellung von (Methoxymethy1endioxypheny1)-, (Dimethoxymethylendioxyphenyl)acroleinen und -pentadienalen und deren h r f i i h r u n g in 4-(Methylendioxyphenyl)-1,3-butadien-l-carbons~uren, 6-(Methylendioxyphenyl)-1,3,5-hexatrien-I carbonsiluren und deren Pyrrolidide bzw. Piperidide wird beschrieben. Derivatives of Methykaedioxybenzew, 391) On Polyenecarboxylic Imides of MethylewdioxybeozeneA generally applicable method for the preparation of (methoxymethy1enedioxy)-, (dimeth-oxymethylenedioxypheny1)acroleins and -pentadienals is described. These compounds are converted into 4-(methylenedioxyphenyl)-1,3-butadienic and 6-(methylenedioxypheny1)-I ,3,5-hexatrienic acids as well as their pyrrolidides and piperidides. Darstellung der PolyencarbonsiiurenDen Polyencarbondureimiden des Methylendioxybenzols und seiner Methoxylogen kommt auf Grund der physiologischen Eigenschaften eine besondere Bedeutung zu 2). Als niedermolekulare sekundiire Pflanzenstoffe wurden hauptslchlich substituierte Zimtsaure-, Phenylpentadien-bzw. Phenylheptatriendure-Abkommlinge isoliert. Wahrend die zur Bildung der verschiedenen Zimtsauren nach Knoevenagel notwendigen Methylendioxybenzaldehyde leicht erhaltlich sind, bereitet die Gewinnung der Phenylacroleine grokre Schwierigkeiten.Die zur Darstellung der Piperinslure-Abkommlinge Id -5d in grokren Mengen benotigten Acroleine lc-5c lieBen sich am gunstigsten nach der von Isled) zur P-Carotinsynthese benutzten Methode bereiten. Aus den leicht darstellbaren Dilthylacetalen 1 a-5a und Athylvinylather entstehen in Gegenwart von Zinkchlorid die zu den Acroleinen 1 c-5c hydrolysierbaren 1,1,3-Triathoxy-3-phenylpropane 1 b-5b.Die Acroleine lc-3c sind im Gegensatz zu anders lautenden Mitteilungena unzer-~~ 1) 38.

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Derivate des Methylendioxybenzols, 6. Mitt.: �ber die Gewinnung und elektrophile Substitutionen des Myristicins�uremethylesters und seiner Derivate

Cited by 6 publications

References 0 publications

Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

A Chemotaxonomic Evaluation ofPetroselinum crispum(Mill.) A. W. Hill (Parsley) Marketed in France

Derivate des Methylendioxybenzols, 39. Über Polyencarbonsäureimide des Methylendioxybenzols

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