14124-36-8

Upstream product

• 27508-87-8 3,5-dimethoxy-2-nitro-toluene 
• 504-15-4 orcinol 

Downstream Products

• 6657-42-7 2-amino-5-methoxy-3-methyl-phenol 
• 204915-77-5 2-(5-methoxy-3-methyl-2-nitrophenyloxy)-N,N-dimethylethanamine 
• 705977-01-1 7-methoxy-3-(4-methoxy-phenyl)-2,5-dimethyl-2H-benzo[1,4]oxazine 
• 122541-98-4 1,5-diacetoxy-2-(2-acetoxy-10-methoxy-4,8,13-trimethyl-benzo[5,6][1,4]oxazino[2,3-b]phenoxazin-3-yl)-3-methyl-benzene 
• 124122-14-1 4-(2-hydroxy-10-methoxy-4,8,13-trimethyl-benzo[5,6][1,4]oxazino[2,3-b]phenoxazin-3-yl)-5-methyl-benzene-1,3-diol 
• 111294-70-3 2-(2,4-dihydroxy-6-methyl-phenyl)-7-methoxy-1,9-dimethyl-phenoxazin-3-one 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship of 3-arylbenzoxazines as selective estrogen receptor β agonists

A series of 3-aryl-7-hydroxybenzoxazine analogues have been prepared and evaluated as ligands for the two estrogen receptor subtypes (ERα and ERβ). From the radioligand binding assay, compounds with more than a 10-fold binding selectivity toward the ERβ s

Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol

Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group.A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring .The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series.They correlated well with ? in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with ?p) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with ρm) for pKa2 (the phenol).A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and ?+ (ρ = -1.1).The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated.It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3 - 5) had measurable rates of reduction. 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that compounds 1, 2, 6 - 9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol.The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.