5586-89-0

Usage

Uses

Used in Pharmaceutical Industry:
Cinnamylamine Hydrochloride is used as a key intermediate compound for the preparation of Tranylcypromine, a drug that acts as a nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). Tranylcypromine is utilized as an antidepressant and anxiolytic agent, helping to alleviate symptoms of depression and anxiety by regulating the levels of certain neurotransmitters in the brain.

InChI:InChI=1/C9H11N.ClH/c10-8-4-7-9-5-2-1-3-6-9;/h1-7H,8,10H2;1H/b7-4+;

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 56866-32-1 2-[(E/Z)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 4360-51-4 cinnamylamine 
• 57294-86-7 (3-azidoprop-1-en-1-yl)benzene 
• 85231-94-3 C₁₈H₂₈NO₅P 
• 146039-13-6 (E)-3-Phenyl-allyl-phosphorimidic acid triethyl ester 

Downstream Products

• 2687-12-9 cinnamyl chloride 
• 1344152-08-4 C₂₃H₂₉NO₉ 

Relevant academic research and scientific papers

Catalytic Staudinger Reduction at Room Temperature

We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.

Direct cycle between co-product and reactant: An approach to improve the atom economy and its application in the synthesis and protection of primary amines

Two important goals of green chemistry are to maximize the efficiency of reactants and to minimize the production of waste. In this study, a novel approach to improve the atom economy of a chemical process was developed by incorporating a direct cycle between a co-product and a reactant of the same reaction. To demonstrate this concept, recoverable 3,4-diphenylmaleic anhydride (1) was designed and used for the atom-economical synthesis of aliphatic primary amines from aqueous ammonia. In each individual cycle, only ammonia and alkyl halide were consumed, and 1 was recovered in nearly a quantitative yield. In this approach for developing atom-economical protecting agents, 1 showed good performance as a recoverable protecting agent for primary amines. The broad substrate scope, good tolerance to various reaction conditions, and high reaction and recovery rates make 1 a valuable complement to conventional primary amine protecting agents.

Amide and amine nucleophiles in polar radical crossover cycloadditions: Synthesis of γ-lactams and pyrrolidines

In this work we present a direct catalytic synthesis of γ-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocata

Quantitative structure inter-activity relationship (QSInAR). Cytotoxicity study of some hemisynthetic and isolated natural steroids and precursors on human fibrosarcoma cells HT1080

Combined experimental and quantitative structure inter-activity relationship (QSIAR) computation methods were advanced in order to establish the structural and mechanistic influences that steroids and triterpenes, either as newly synthesized or naturally isolated products, have on human HT1080 mammalian cancer cells. The main Hansch structural indicators such as hydrophobicity (LogP), polarizability (POL) and total energy (Etot) were considered and both the structure-projected as well as globally computed correlations were reported; while the inter-activity correlation of the global activity with those projected on structural information was revealed as equal to the direct structural-activity one for the trial sets of compounds, the prediction for the testing set of molecules reported even superior performances respecting those characteristic for the calibration set, validating therefore the present QSInAR models; accordingly, it follows that the LogP carries the most part of the cytotoxic signal, while POL has little influence on inhibiting tumor growth-A complementary behavior with their earlier known influence on genotoxic carcinogenesis. Regarding the newly hemisynthetic compounds it was found that stigmasta-4,22-dien-3-one is not adapted for cell membrane diffusion; it is recommended that aminocinnamyl chlorohydrate be further modified in order to acquire better steric influence, while aminocinnamyl-2,3,4,6-O- tetraacetyl-a-D-glucopyranoside was identified as being inhibited in the tumor cell by other molecular mechanisms-here not revealed-although it has a moderate-high anti-cancer structurally predicted activity.

N-(diethoxyphosphoryl)aldimines as synthetic equivalents of A1 type synthons

Novel organophosphorus reagents useful for convergent synthesis of primary amines are presented.