51498-40-9

Usage

Uses

Used in Scientific Research:
4DAMP is used as a research chemical for studying the muscarinic acetylcholine receptor. Its ability to block the binding of certain ligands to these receptors aids in understanding the physiological and pharmacological effects of muscarinic acetylcholine signaling.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 4DAMP is used as a starting point for the development of new drugs targeting the muscarinic acetylcholine receptor system. Its antagonistic properties make it a promising candidate for creating medications that can modulate or inhibit the receptor's activity, potentially leading to treatments for various conditions related to this receptor system.
Used in Drug Discovery and Design:
4DAMP is also utilized in drug discovery and design processes, where its interaction with the muscarinic acetylcholine receptor can provide insights into the receptor's structure and function. This information can be crucial for the development of more effective and targeted drugs that can specifically bind to and modulate the receptor's activity.

Upstream product

• 50-00-0 formaldehyd 
• 122333-64-6 trans-N-Methyl-5-phenyl-4-penten-1-amine 
• 118087-39-1 2-Methyl-1,3,4,5,6,11a-hexahydro-2H-2-benzazonine 
• 118087-37-9 1-Methyl-2-phenyl-1-trimethylsilanylmethyl-piperidinium; iodide 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 
• 19070-16-7 3-(N,N-dimethylamino)propylmagnesium chloride 
• 103-64-0 bromostyrene 
• 51498-40-9 trans-N,N-dimethyl-5-phenyl-4-penten-1-amine 
• 100-52-7 benzaldehyde 
• 83299-97-2 bromure de N,N-dimethylamino-4 butyltriphenylphosphonium 
• 3466-80-6 2-phenylpiperidine 
• 118087-36-8 2-Phenyl-1-trimethylsilanylmethyl-piperidine 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 

Downstream Products

• 55666-19-8 E-1-Trimethylammonio-5-phenylpenten-4 
• 51498-40-9 cis-N,N-dimethyl-5-phenyl-4-penten-1-amine 
• 62101-01-3 N,N-dimethyl-5-phenylpentan-1-amine 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 3909-96-4 (1E,3E)-1-phenyl-1,3-pentadiene 

Relevant academic research and scientific papers

Iron thiolate complexes: Efficient catalysts for coupling alkenyl halides with alkyl grignard reagents

Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required. Copyright

Direct aminoalkylation of arenes, heteroarenes, and alkenes via Ni-catalyzed Negishi cross-coupling reactions

A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (±)-galipinine and (±)-cusparine, is also reported.

Chain-length- and solvent-dependent intramolecular proton transfer in styrene-amine exciplexes

The photochemical and photophysical behavior of several ((N,N-dimethylamino)alkyl)styrenes in which the amino group is attached to the styrene α- or β-carbon by a methyl, ethyl, propyl, or butyl polymethylene chain has been investigated. Efficient intramolecular addition of an aminomethyl C-H to styrene is observed in nonpolar solvents for the (aminoethyl)styrenes, and addition of an aminomethylene C-H is observed for the (aminobutyl)styrenes. However, the (aminoethyl)- and (aminopropyl)styrenes do not undergo intramolecular addition reactions. Both the reactive and unreactive (aminoalkyl)styrenes form fluorescent singlet exciplexes in nonpolar and polar solvents. The resuls of exciplex and product quenching by an added primary amine indicate that the fluorescent exciplex is an intermediate in the addition reactions of the (aminoalkyl)styrenes. Activation parameters for both exciplex formation and exciplex proton transfer have been determined. Highly regioselective intramolecular proton transfer is proposed to occur via least motion pathways from the lowest energy folded conformations of the singlet exciplex intermediates in nonpolar solvents. The solvent dependence of exciplex proton transfer, fluorescence, intersystem crossing, and nonradiative decay is attributed to a change in exciplex conformation from folded in nonpolar solvents to extended in solvents more polar than diethyl ether.

Photophysical and photochemical behavior of intramolecular-styrene-amine exciplexes

The photophysical and photochemical behavior of a series of secondary and tertiary ω-(β-styryl)aminoalkanes with one to five methylenes separating the styryl and amino groups has been investigated and compared to the intermolecular reactions of 1-phenylpropene with secondary and tertiary amines. The tertiary styrylamines form fluorescent intramolecular exciplexes, but fail to undergo intramolecular addition reactions. Both the rate constant for exciplex formation and the stability of the exciplex are dependent upon the length of the polymethylene chain connecting the chromophores. The failure of the tertiary amine exciplexes to undergo intramolecular addition is attributed to an unfavorable exciplex geometry for α-C-H transfer to the styrene double bond. While the secondary styrylamines do not form fluorescent exciplexes, the dependence of the styrene singlet lifetime upon the polymethylene chain length is similar to that for the tertiary styrylamines. Intramolecular N-H addition to the styrene double bond results in the formation of two regioisomeric (α-phenyl and α-benzyl) cyclic amines of different ring size. The regioisomer of larger ring size is favored except in the case in which four methylenes separate the chromophores. The effects of polymethylene chain length, solvent polarity, temperature, and the bulk of the N-alkyl group upon product yields and ratios are discussed in terms of a mechanism involving singlet exciplex and biradical intermediates.

Rearrangement of 1-Methyl-2-(substituted-phenyl)piperidinium 1-Methylides in a Neutral Medium

Reaction of 1-methyl-1--2-(substituted-phenyl)piperidinium iodides (3) with cesium fluoride in DMF gave good yields of 2-methyl-1,3,4,5,6,11a-hexahydro-2H-2-benzazonine derivatives (5), which are regarded as unstable intermediates

A Stable Intermediate in the Sommelet-Hauser Rearrangement of 1-Methyl-2-phenyl-piperidinium 1-Methylides: The Improved Sommelet-Hauser Rearrangement

Reaction of 1-methyl-1-(trimethylsilyl)methyl-2-(substituted phenyl)piperidinium iodides (2) with caesium fluoride gave high yields of 2-methyl-1,3,4,5,6,11a-hexahydro-2H-2-benzazonines (4) which are regarded as unstable intermediates in the Sommelet-Haus

ANOMALOUS STEREOCHEMISTRY IN THE WITTIG REACTION INDUCED BY NUCLEOPHILIC GROUPS IN THE PHOSPHONIUM YLIDE

Reaction of ylides from 3-9 with benzaldehyde show that carboxylate and oxido functionalities proximate to the ylide center promote anomalously high E stereoselectivity in alkene formation.Through the use of α-deuterated ylides 12-14, an internal "trans-selective Wittig" mechanism was ruled out as a principal source of exaggerated E alkene production.