271250-53-4

Basic information

• Product Name: 7-chloro-2-iodo-5,8-dimethoxy-1-methoxymethoxy-3-[(3-p-methoxyphenyl-2-propynoyloxy)methyl]naphthalene
• Synonyms: 7-chloro-2-iodo-5,8-dimethoxy-1-methoxymethoxy-3-[(3-p-methoxyphenyl-2-propynoyloxy)methyl]naphthalene
• CAS NO: 271250-53-4
• Molecular Weight: 596.803
• Mol File: 271250-53-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7-chloro-2-iodo-5,8-dimethoxy-1-methoxymethoxy-3-[(3-p-methoxyphenyl-2-propynoyloxy)methyl]naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-2-iodo-5,8-dimethoxy-1-methoxymethoxy-3-[(3-p-methoxyphenyl-2-propynoyloxy)methyl]naphthalene(271250-53-4)
• EPA Substance Registry System: 7-chloro-2-iodo-5,8-dimethoxy-1-methoxymethoxy-3-[(3-p-methoxyphenyl-2-propynoyloxy)methyl]naphthalene(271250-53-4)

Safety Data

• Hazardous Substances Data: 271250-53-4(Hazardous Substances Data)

Upstream product

• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 241149-23-5 7-chloro-3-hydroxymethyl-2-iodo-5,8-dimethoxy-1-(methoxymethoxy)naphthalene 
• 241149-22-4 3-acetoxymethyl-7-chloro-2-iodo-5,8-dimethoxy-1-(methoxymethoxy)naphthalene 
• 241149-21-3 3-acetoxymethyl-7-chloro-2-iodo-5,8-dimethoxy-1-naphthol 
• 241149-20-2 3-acetoxymethyl-7-chloro-5,8-dimethoxy-1-naphthol 
• 152039-15-1 6-Chloro-4-hydroxy-5,8-dimethoxy-2-(hydroxymethyl)naphthalene 

Downstream Products

• 337975-30-1 3-benzoyloxy-7-chloro-5,8-dimethoxy-1-(methoxymethoxy)-2-(3-p-methoxyphenyl-2-propynoyl)naphthalene 
• 337975-23-2 7-chloro-3-hydroxymethyl-5,8-dimethoxy-1-(methoxymethoxy)-2-(3-p-methoxyphenyl-2-propynoyl)naphthalene 

Relevant articles and documents

Synthesis of espicufolin based on 6-endo ring closure of o-alkynoylnaphthols

Regioselective halogenation of 3-acetoxymethyl-7-chloro-5,8-dimethoxy-1-naphthol 5 was achieved by DBH or I2/N-methylmorpholine to give the corresponding 2-halogeno-1-naphthols 8 and 11, which were converted to 1-methoxymethoxy-3-(alk-2-ynoyloxymethyl)-2-halogenonaphthalenes 17 and 18 in good yields. An intramolecular acyl-transfer reaction of the 2-halogenonaphthalenes triggered by halogen-lithium exchange with BuLl at -78 °C gave 1-methoxymethoxy-2-alkynoyl-3-(hydroxymethyl)naphthalenes 21 in high yields. After protection of the hydroxymethyl group as a benzoate, formation of a γ-pyrone ring was easily achieved by deprotection of the methoxymethyl group followed by spontaneous 6-endo ring closure under mildly acidic conditions. The pyrone derivative having a 1-methylpropyl group was successfully converted to espicufolin 1.