77785-12-7

Basic information

• Product Name: 5,7-dimethoxy-13-methyl-13,14-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine
• Synonyms: Dihydromacarpine
• CAS NO: 77785-12-7
• Molecular Formula: C₂₂H₁₉NO₆
• Molecular Weight: 393.3894
• Mol File: 77785-12-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 633.5°C at 760 mmHg
• Flash Point: 191.3°C
• Density: 1.396g/cm³
• Vapor Pressure: 5.91E-16mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 5,7-dimethoxy-13-methyl-13,14-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dimethoxy-13-methyl-13,14-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine(77785-12-7)
• EPA Substance Registry System: 5,7-dimethoxy-13-methyl-13,14-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine(77785-12-7)

Safety Data

• Hazardous Substances Data: 77785-12-7(Hazardous Substances Data)

Upstream product

• 10022-35-2 1-bromo-2-methoxy-4,5-methylenedioxybenzene 
• 168098-72-4 4-methoxy-2-(2-methoxy-4,5-methylenedioxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene 
• 673477-43-5 1-ethynyl-2-methoxy-4,5-methylenedioxybenzene 
• 77784-67-9 (5-Bromo-6-methoxy-benzo[1,3]dioxol-4-ylmethyl)-(8-methoxy-naphtho[2,3-d][1,3]dioxol-5-yl)-amine 
• 77784-66-8 [1-(5-Bromo-6-methoxy-benzo[1,3]dioxol-4-yl)-meth-(Z)-ylidene]-(8-methoxy-naphtho[2,3-d][1,3]dioxol-5-yl)-amine 
• 125032-01-1 oxymacarpine 
• 64-18-6 formic acid 
• 77785-13-8 C₂₁H₁₅NO₆ 
• 17889-56-4 macarpine chloride 

Relevant articles and documents

NEW FINDINGS IN BISCHLER-NAPIERALSKI REACTION: FORMATION OF 12-AZONIANAPHTHAZULENES FROM 2-ARYL-1-NAPHTHYLFORMAMIDES AND THEIR UNEXPECTED TRANSFORMATION INTO BENZINDOLES THROUGH HYDRIDE REDUCTION

The Bischler-Napieralski Reaction (BNR) of N--N-methylformamides using POCl3 abnormally gave 12-azonianaphthazulene derivatives, which could be effectively transformed into benzindoles with a 1-alkoxy-8-oxabicyclooct-2-ene skeleton through hydride reduction, as additional cyclized products.In contrast, the BNR of naphthylformamides with methoxy groups in place of a methylenedioxy function at the same position in the phenyl ring led to normal cyclization to give benzophenanthridinium chlorides quantitatively.The speculative mechanism for the abnormal BNR and the indole formation will be discussed.

Anomalous substituent effects in the Bischler-Napieralski reaction of 2-aryl aromatic formamides

Treatment of some 1-naphthylformamides (or formanilides) possessing a 2,4,5-trioxygenated phenyl substituent at the 2-position with POCl3 caused an unprecedented carbon insertion reaction into a benzene ring, producing 7-5 ring (azaazulene) systems as valence isomers of isoquinoline skeletons. Precise examination of this abnormal Bischler-Napieralski reaction (BNR) using various substrates led to the following scope and limitations: (i) the 7-5 ring systems were constructed when either 2-alkoxy-4,5-methylenedioxyphenyl- or 4,5-dialkoxy-2-hydroxyphenyl-substituted formamides were used as a starting substrate; (ii) in the former case the formyl carbon was inserted into the C1-C6 bond of the 2-phenyl group, and normal isoquinoline cyclization competed with an abnormal carbon insertion reaction; (iii) the presence of a hydroxy group at the 2′-position as in the latter cases caused exclusive carbon insertion, in which alternative C1-C2 insertion products were quantitatively formed; (iv) 3,6-dimethoxy-2-hydroxyphenyl-substituted formanilide electronically equivalent to 4,5-dialkoxy-2-hydroxy derivatives produced an indole-pyrone as an abnormal BNR product. Theoretical approaches using the PM-3 method indicated that these abnormal BNRs could be triggered by ipso attack at the 1′-position yielding spiro intermediates. Ring cleavege of the six-membered ring in the spiro intermediates to a ketene function followed by recyclization was proposed for the 2′-hydroxy-directed abnormal BNRs leading to the C1-C2 insertion product or the indole-pyrone derivative.

Chemical transformation of protoberberines. XVI. Regioselective introduction of an oxy functionality at the C12-position of the benzo[c]phenanthridine skeleton: A convenient synthesis of macarpine from oxychelirubine

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