573-13-7

Usage

Contact allergens

Lapachenol is contained in the heart-wood of Lapacho wood (Tabebuia avellanedae Lorentz, Bignoniaceae family). It is a secondary allergen, after lapachol and deoxylapachol, and likely a prohapten transformed in vivo into a quinone hapten.

InChI:InChI=1/C16H16O2/c1-16(2)9-8-11-10-14(17-3)12-6-4-5-7-13(12)15(11)18-16/h4-10H,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 24052-01-5 6-methoxy-7,8-benzocoumarin 
• 181364-86-3 4-Methoxy-naphthyl-⁽¹⁾-(1,1-dimethyl-propargyl)-aether 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 84-85-5 4-methoxynaphth-1-ol 
• 101431-60-1 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromen-4-ol 
• 909576-35-8 5-bromo-6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran 
• 79-22-1 methyl chloroformate 
• 909576-31-4 2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone 
• 645413-83-8 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol 
• 909576-32-5 2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3,6-diol 
• 909576-33-6 5-bromo-6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol 
• 909576-34-7 5-bromo-6-methoxy-2,2-dimethyl-3-tosyloxy-3,4-dihydro-2H-naphtho[1,2-b]pyran 
• 3568-90-9 deoxylapachol 

Downstream Products

• 102598-69-6 6-methoxy-2,2-dimethyl-2,3-dihydro-benzo[h]chromen-4-one-(2,4-dinitro-phenylhydrazone) 
• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 4707-33-9 α-lapachone 
• 15297-92-4 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 
• 20213-26-7 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene 

Relevant academic research and scientific papers

Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a

Mollugin derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient

The present invention relates to mollugin derivatives, an optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient. The mollugin derivatives of the present invention become salts easily by introducing an amine group, so that a solubility improvement effect is remarkable compared to existing poorly-soluble substances, and in the case of treatment with the mollugin derivatives, the activity of inhibiting the adhesion of U937 cells, which are monocytic cells, in TNF-andalpha; or IL-6-inducible HT-29 cells was excellent, thereby being useful as pharmaceutical compositions for prevention or treatment of inflammatory bowel disease.(AA) Example 7 (10 andmu;M)(BB) Example 21 (10 andmu;M)COPYRIGHT KIPO 2017

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation- esterification process at 120-130°C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2- ones were obtained in 5-85% yields.

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 °C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields.

Simultaneous synthesis of both rings of chromenes via a benzannulation/ o -quinone methide formation/electrocyclization cascade

A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in the emergence of a chromene upon an electrocyclization. This reaction was extended to provide access by employing an aryl carbene complex. This constitutes the first synthesis of chromenes in which both rings of the chromene system are generated in a single step and is highlighted in the synthesis of lapachenole and vitamin E.

Synthesis of hemitectol, tectol, and tecomaquinone i

The first total syntheses of Tectona grandis (teak) natural products hemitectol and tectol are described. The observation of spontaneous dimerisation of hemitectol to tectol suggests the monomer is the true natural product and that the dimer is an artifact of isolation. Georg Thieme Verlag KG · Stuttgart · New York.

Concise synthesis of (±)-rhinacanthin A, dehydro α-lapachone, and β-lapachone, and pyranonaphthoquinone derivatives

A concise synthesis of (±)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-α-lapachone, followed by chemo-and regioselective reduction. Dehydro-α-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. β-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4- naphthoquinone.

A novel method for the synthesis of substituted benzochromenes by ethylenediamine diacetate-catalyzed cyclizations of naphthalenols to α,β-unsaturated aldehydes. Concise synthesis of the natural products lapachenole, dihydrolapachenole, and mollugin

A new synthetic route for biologically interesting benzochromenes was developed starting from naphthalenols and α,β-unsaturated aldehydes in the presence of ethylenediamine diacetate. This methodology was applied for the total synthesis of the biologicall

Synthesis of mollugin

The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented.

Two expedient syntheses of β-lapachone

Two short syntheses of β-llapachone (1) from readily available naphthols 2a,b and 3-methylbut-2-enal via a mild phenylboronic acid-mediated cyclization to 2H-chromenes 3a,b is reported.