66192-02-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 2623, 1950 DOI: 10.1021/ja01162a078

Upstream product

• 66192-15-2 2-(2-Bromo-5-methoxy-benzyl)-malonic acid diethyl ester 
• 621-54-5 3-(3-hydroxyphenyl)-propanoic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 6099-04-3 3-methoxycinnamic acid 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 

Downstream Products

• 5411-61-0 4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-one 
• 135064-20-9 cis-5-methoxy-2-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine 
• 135064-20-9 trans-5-methoxy-2-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine 

Relevant academic research and scientific papers

Grob-Type Fragmentation Releases Paracyclophane Ring Strain in a Late-Stage Precursor of Haouamine A

A ketene [2 + 2]-addition, an intramolecular aldol reaction, a Suzuki-Miyaura coupling, and a chemoselective lactam reduction were used to prepare a late-stage precursor of haouamine A. Exposure to acid led to a Grob-type fragmentation of the strained 3-aza[7]paracyclophane ring, followed by a tandem Pictet-Spengler reaction of the intermediate iminium ion and conversion to a novel 1,4a-propanocyclopenta[b]pyridine. This cascade reaction might also be relevant for the mechanism of action of the natural product.

Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)-H Bond Functionalization

Herein we report a diastereoselective synthesis of medium-sized carbocycle-fused piperidines via [1,n (n = 6, 7)]-[1,5]-sequential hydride shift triggered double C(sp3)-H bond functionalization. When cinnamylidene malonates having N,N-dibenzyl propylamine moiety were treated with 5 mol % of Yb(OTf)3, a [1,6]-[1,5]-sequential hydride shift/cyclization process proceeded to afford seven-membered carbocycle-fused piperidines with excellent diastereoselectivities. This sequential system was applicable to the synthesis of eight-membered carbocycle-fused piperidines by an unprecedented [1,7]-[1,5]-sequential hydride shift/cyclization process.

Construction of seven-and eight-membered carbocycles by Lewis acid catalyzed C(sp3)-H bond functionalization

We achieved a concise construction of seven-and eight-membered carbocycles via Lewis acid catalyzed C(sp3)-H bond functionalization. In these reactions, a quite rare [1,6 (or 7)]-hydride shift/cyclization process proceeded smoothly to afford seven-and eight-membered carbocycles with good chemical yields starting from substrates with high conformational freedom.

Highly efficient gold-catalyzed synthesis of dibenzocycloheptatrienes

Dibenzocycloheptatrienes are obtained by a gold-catalyzed 7-exo-dig hydroarylation protocol in a highly efficient manner. The gold-catalyzed reaction usually gives the products in high yields and excellent selectivity. This procedure provides an easy and

Synthesis and structure activity relationships of cis- and trans- 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridines for 5-HT receptor subtypes

A series of cis- and trans-fused hexahydroindeno[2,1-c]pyridines have been prepared and evaluated for affinity and selectivity at the 5-HT(1A) subtype of the serotonin receptor. Using molecular modeling studies we predicted that the 5-methoxy-trans-fused