95417-67-7

Upstream product

• 134697-63-5 1'-benzyl-3,4-dihydro-2-oxospiro 
• 55-51-6 N,N-bis(2-chloro-ethyl)-benzenemethanamine 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 134697-64-6 4-(tetralinyl)piperidine 
• 100-39-0 benzyl bromide 
• 15971-29-6 4-methoxy-1-naphthaldehyde 
• 95449-63-1 9b-(N-benzylcarbamoylmethyl)-1,2,3a,4,5,9b-hexahydronaphtho<2,1-b>furan-2-one 
• 95417-65-5 1-benzylspiro-2'-ol 
• 95449-62-0 1,2,3a,4,5,9b-hexahydro-9b-(methoxycarbonylmethyl)naphtho<2,1-b>furan-2-one 
• 95417-64-4 1,1-bis(methoxycarbonylmethyl)-2-tetralone 
• 95417-66-6 1'-benzylspiro<(1,4-dihydronaphthalene)-1,4'-piperidine> 

Downstream Products

• 134697-85-1 C₂₁H₂₄N₂O₂ 
• 134697-73-7 C₂₂H₂₇NO 
• 134697-87-3 C₂₁H₂₄ClN 
• 134697-75-9 C₂₂H₂₇N 
• 134697-81-7 C₂₂H₂₇N 
• 134697-83-9 1'-cyclohexylmethyl-3,4-dihydrospiro(naphthalene-1(2H),4'-piperidine) 

Relevant academic research and scientific papers

Synthesis of benzo-fused spiropiperidines through a regioselective free radical-mediated cyclization as key step: a suitable alternative towards the lead σ-1 receptor ligand L-687384

Abstract The synthesis of four novel benzo-fused spiropiperidines and the lead σ-1 receptor ligand L-687384 through a xanthate-mediated free radical spirocyclization as key step is described. Furthermore, the key free radical-based cyclization was computa

Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites

We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.

Spiropiperidines as high-affinity, selective σ ligands

A variety of achiral conformationally restricted spirocyclic piperidines have been prepared in an attempt to investigate the functional role of the central σ recognition site. All the compounds possessed a lipophilic N- substituent incorporating either a tetralin, indan, or benzocycloheptane skeleton. Their in vitro affinity at the σ site was assessed in radioligand displacement experiments with guinea pig cerebellum homogenates using the σ- specific radioligand [3H]-N,N'-di-o-tolylguanidine ([3H]-DTG, [3H]-6). A study of the structure-activity relationships identified the N-butyl and N- dimethylallyl substituents as the optimum groups for high affinity and selectivity at the σ site (e.g., 3,4-dihydro-1'-(3-methylbut-2- enyl)spiro[1H-indene-1,4'-piperidine] (48), pIC50 = 8.9 vs [3H]-6 and greater than 10 000-fold selective over the dopamine D2 receptor). Such compounds are amongst the highest affinity σ ligands reported to date, with excellent selectivity over the dopamine D2 receptor, and may serve as a useful tool for exploring the physiological role of the σ site.

Synthesis and structure-activity relationship of spiro[isochroman-piperidine] analogs for inhibition of histamine release. IV

Various 1'-(o, m, and/or p-substituted benzyl) (5), 1'-(heterocyclic arylmethyl) (6), and 1'-acyl (7) analogs of spiro[isochroman-3,4'-piperidin]-1-one were prepared and tested for inhibitory activity on the compound 48/80-induced release of histamine from mast cells. The biological results suggested that the activity is mainly affected by the lipophilicity rather than by the electrostatic character of the 1'-substituent. 4-Benzylspiro[cyclohexane-1,3'-hexahydroisochroman]-1'-one (17) and 9-benzyl-1-oxa-spiro[5.5]undecan-2-one (18) were prepared and found to be inactive, implying that the benzene moiety in the isochroman ring is essential for the activity.