105310-66-5

Basic information

• Product Name: Cyclopropanecarbonyl chloride, 2-(bromomethyl)-1-phenyl-, cis-
• CAS NO: 105310-66-5
• Molecular Formula: C11H10BrClO
• Molecular Weight: 273.557
• Mol File: 105310-66-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarbonyl chloride, 2-(bromomethyl)-1-phenyl-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarbonyl chloride, 2-(bromomethyl)-1-phenyl-, cis-(105310-66-5)
• EPA Substance Registry System: Cyclopropanecarbonyl chloride, 2-(bromomethyl)-1-phenyl-, cis-(105310-66-5)

Safety Data

• Hazardous Substances Data: 105310-66-5(Hazardous Substances Data)

Upstream product

• 69160-63-0 (1S,2R)/(1R,2S)-2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid 

Downstream Products

• 105310-90-5 (Z)-1-phenyl-2-(bromomethyl)-N,N-diethylcyclopropanecarboxamide 
• 105310-48-3 methyl (+/-)-cis-2-(bromomethyl)-1-phenylcyclopropanecarboxylate 
• 105310-49-4 ethyl (+/-)-cis-2-(bromomethyl)-1-phenylcyclopropanecarboxylate 
• 105310-75-6 (1SR,2RS)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane carboxamide 
• 105310-26-7 (Z)-1-phenyl-2-<(4-methylpiperazinyl)methyl>-N,N-diethylcyclopropanecarboxamide 
• 105310-23-4 (+/-)-(Z)-1-phenyl-2-<(N-methylamino)methyl>cyclopropane-N,N-diethylcarboxamide 
• 105310-09-6 milnacipran 
• 105310-07-4 (1R,2S)-2-Aminomethyl-1-phenyl-cyclopropanecarboxylic acid ethylamide 
• 105310-08-5 (1S,2R)-2-Aminomethyl-1-phenyl-cyclopropanecarboxylic acid dimethylamide 
• 105310-06-3 2-(aminomethyl)-1-phenylcyclopropanecarboxamide 
• 105310-95-0 (1R,2S)-2-{[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-methyl}-1-phenyl-cyclopropanecarboxylic acid diethylamide 
• 105310-73-4 (1S,2R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1-phenyl-cyclopropanecarboxylic acid ethylamide 
• 105310-74-5 (1S,2R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1-phenyl-cyclopropanecarboxylic acid dimethylamide 
• 105310-72-3 (1S,2R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1-phenyl-cyclopropanecarboxylic acid amide 

Relevant articles and documents

Synthesis of (+)- and (-)-cis-2-[(1-adamantylamino)-methyl]-1-phenylcyclopropane derivatives as high affinity probes for σ1 and σ2 binding sites

Selective ligands for either sigma1 (σ1) or σ2 binding sites are potentially useful for gaining a better understanding of the physiological functions of these proteins. Moreover, potent and selective homochiral σ1/su

Substituted 1-phenyl-2-cyclopropylmethylamines with high affinity and selectivity for sigma sites

A series of 1-phenyl-2-cyclopropylmethylamines structurally related to (+)- and (-)-MPCB were synthesized and their binding affinities for σ1, σ2, opioid and dopamine (D2) receptors were evaluated. Substitution of the cis-N-normetazocine with different aminic moieties provided compounds with high affinity and selectivity for σ binding sites with respect to opioid and dopamine (D2) receptors. The observed increase in σ2 affinity as compared to the parent (+)-MPCB, supports the idea that the particular stereochemistry of (+)-cis-N-normetazocine affects σ1 selectivity but does not affect σ1 affinity. The (±)-cis isomers of methyl 2-[(1-adamantylamino)methyl]-1-phenylcyclopropane-1-carboxylate (18) displayed a higher affinity and selectivity for the σ1 and σ2 receptor subtypes compared to the (±)-trans 19. Interestingly, the enantiomer (-)-cis 18 displayed a preference for σ1 receptor subtype whereas the (+)-cis 18 did for σ2. These results prompt us to synthesize compounds with modification of nitrogen and carboxyl groups. The compounds obtained showed high affinities and selectivity for σ sites. Moreover, modifications of carboxyl groups provided compounds with the highest affinities in the series. In particular, compound 25 with reverse-type ester showed a K(i) of 0.6 and 4.05nM for σ1 and σ2 binding sites, respectively. Copyright (C) 2000 Elsevier Science Ltd.