1459-62-7

Usage

InChI:InChI=1/C14H18N4O4/c19-17(20)12-8-9-13(14(10-12)18(21)22)16-15-11-6-4-2-1-3-5-7-11/h8-10,16H,1-7H2

Upstream product

• 696-71-9 cyclooctanol 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 73674-22-3 14-methyl-5,5-dioxo-5,7,8,9,10,11,12,14-octahydro-6H-5λ⁶-thia-14-aza-benzocyclododecen-13-one 
• 73674-12-1 7,8,9,10,11,12-hexahydro-4-methyl-2,3-benzo-1-thia-4-azacyclododecen-5(6H)-one 
• 78082-10-7 bis<2-phenyl> disulfide 
• 73674-09-6 8-bromo-n-octanoyl chloride 
• 73674-32-5 2-(2-Methylaminophenylsulfonyl)-cyclooctanon 
• 17696-11-6 8-bromooctanoic acid 
• 502-49-8 cycloactanone 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

2-Iodoxybenzoic acid organosulfonates: Preparation, X-ray structure and reactivity of new, powerful hypervalent iodine(v) oxidants

New powerful hypervalent iodine(v) oxidants, tosylate and mesylate derivatives of 2-iodoxybenzoic acid (IBX), were prepared by the reaction of IBX with the corresponding sulfonic acids. Single crystal X-ray crystallography of the diacetate derivative of IBX-tosylate revealed an unusual heptacoordinated iodine geometry without any significant intermolecular secondary interactions.

Medium-ring Ketone Synthesis. Synthesis of Eight- to Twelve-membered Cyclic Ketones based on the Intramolecular Cyclization of Large-Membered Lactam Sulfoxides or Sulfones

An effective general method for the construction of medium-ring ketones from the corresponding ω-bromocarboxylic acids is described.When the diamide disulfide 10 was treated with NaBH4 and NaH in 2-propanol, reductive cleavage of the sulfur-sulfur bond and concomitant intramolecular coupling of the resulting thiolate anion with the terminal bromide took place and the large-ring lactam sulfide 7, which was the key intermediate for the synthesis of medium-ring ketones, was obtained.Although lithium diisopropyl amide (LDA) treatment of 11 followed by reductive desulfurization provided cycloundecanone (13d) in only 19.5percent yield, intramolecular cyclization of the α-methylated analogues 17 with LDA proceeded smoothly and the keto sulfoxides 18 were obtained in quantitative yields.In the case of the lactam sulfones 21, tert-BuOK was effective as a base for the intramolecular cyclization, affording the keto sulfones 22 in quantitative yields.The keto sulfoxides 18 and sulfones 22 were subjected to reductive desulfurization with Al-Hg to yield medium-ring ketones 19 and 13, respectively, in high yields.Keywords - medium-ring ketone; intramolecular cyclization; large-ring lactam sulfide; bis(2-methylaminophenyl) disulfide; 2-methylaminobenzenethiol; reductive desulfurization; sulfur-stabilized carbanion; active methylene