143654-03-9

Basic information

• Product Name: Benzene, 2-methoxy-1-(methoxymethoxy)-4-(2-propenyl)-
• CAS NO: 143654-03-9
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Mol File: 143654-03-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, 2-methoxy-1-(methoxymethoxy)-4-(2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 2-methoxy-1-(methoxymethoxy)-4-(2-propenyl)-(143654-03-9)
• EPA Substance Registry System: Benzene, 2-methoxy-1-(methoxymethoxy)-4-(2-propenyl)-(143654-03-9)

Safety Data

• Hazardous Substances Data: 143654-03-9(Hazardous Substances Data)

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 1730-25-2 allylmagnesium bromide 
• 16766-30-6 4-Chloroguaiacol 
• 90-05-1 2-methoxy-phenol 
• 97-53-0 4-allylguaiacol 
• 107-30-2 chloromethyl methyl ether 
• 109-87-5 Dimethoxymethane 

Downstream Products

• 75225-33-1 [1-(8-propenyl)-3-[1′-(8′-propenyl)-3′-methoxyphenoxy]-4-hydroxy-5-methoxybenzene] 
• 143654-10-8 (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-one 
• 143654-10-8 (3E,10E)-(R)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-one 
• 143654-09-5 (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol 
• 143654-09-5 (3E,10E)-(R)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol 

Relevant articles and documents

Synthesis and Structure-Activity Relationship of Dehydrodieugenol B Neolignans against Trypanosoma cruzi

Trypanosoma cruzi is the etiologic agent of Chagas disease, which affects over seven million people, especially in developing countries. Undesirable side effects are frequently associated with current therapies, which are typically ineffective in the treatment of all stages of the disease. Here, we report the first synthesis of the neolignan dehydrodieugenol B, a natural product recently shown to exhibit activity against T. cruzi. Using this strategy, a series of synthetic analogues were prepared to explore structure-activity relationships. The in vitro antiparasitic activities of these analogues revealed a wide tolerance of modifications and substituent deletions, with maintained or improved bioactivities against the amastigote forms of the parasite (50% inhibitory concentration (IC50) of 4-63 μM) and no mammalian toxicity (50% cytotoxic concentration (CC50) of >200 μM). Five of these analogues meet the Drugs for Neglected Disease Initiative (DNDi) "hit criteria"for Chagas disease. This work has enabled the identification of key structural features of the natural product and sites where scaffold modification is tolerated.

Synthetic method of eugenol

A synthetic method of eugenol comprises the following steps of: dropwise adding a halogenating reagent into guaiacol, adding an alkaline saturated solution for layering, washing with water, drying, filtering, and carrying out reduced pressure distillation to obtain 4-halogen-2-methoxyphenol; adding 4-halogen-2-methoxyphenol and alkali into an organic solvent, adding alkyl halide alkyl ether, adding water, layering, extracting the water layer with a solvent, drying the organic layer, filtering, and removing the solvent to obtain 4-halogen-2-methoxy-1-alkoxy alkylphenol; dropwise adding 4-halogen-2-methoxy-1-alkoxy alkylphenol into an ether solution of allyl magnesium halide; adding an ammonium chloride aqueous solution to obtain a mixture, carrying out reduced pressure distillation to remove ether, carrying out water layer extraction, combining ethyl acetate layers, drying, filtering, and carrying out reduced pressure distillation to obtain 4-allyl-2-methoxy-1-alkoxy alkylphenol; and mixing the product with p-toluenesulfonic acid monohydrate, stirring, carrying out reduced pressure distillation, and carrying out high vacuum distillation to obtain eugenol. The defects that in the prior art, guaiacol directly reacts with 3-chloropropene, so that ortho-position reaction is easier, and the para-position product yield is low and does not exceed 50% are overcome.

A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach

Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.