14475-60-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 6651, 1988 DOI: 10.1016/S0040-4039(00)82421-1

Upstream product

• 31058-09-0 4-methylamino-butyronitrile 
• 18807-73-3 N-benzyloxycarbonyl-1,4-butanediamine hydrochloride 
• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 103-67-3 benzyl-methyl-amine 
• 50-00-0 formaldehyd 
• 110-60-1 1,4-diaminobutane 
• 7544-87-8 2-Methylimino-pyrrolidin-hydrochlorid 

Downstream Products

• 1384353-29-0 C₃₃H₄₅N₃O₄ 
• 120-94-5 1-Methylpyrrolidine 

Relevant academic research and scientific papers

Enzymatic aminopropylation of certain secondary amines

Two unusual aminopropyl acceptors found in a survey of putrescine binding sites of mammalian spermidine synthase, N-methylputrescine (I) and 4-aminomethylpiperidine (II), were examined for their aminopropyl derivatives. Studies under In vitro incubation conditions suggested that the aminopropyl derivatives of the secondary amine of I and II, N4-methylspermidine (Is) and 1-N-(3-aminopropyl)-4-aminomethylpiperidine (IIs), and of the primary amine of I and II, N8-methy]spermidine (Ip) and 4-[N-(3-aminopropyl)aminomethyl]piperidine (IIp), respectively, were biosynthesized by rat spermidine synthase. Studies on the cell culture system of cultured rat hepatoma (HTC) cells treated with α-difluoromethylornithine, an ornithine decarboxylase inhibitor, clearly showed the presence of Is and Ip when I was administered, and IIs and IIp when II was administered, with no detection of putrescine or spermidine. These results suggested that mammalian spermidine synthase can transfer the anunop}opyl moiety of decarboxylated S-adenosylmethionine to certain secondary amines in living cells.

A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events

Heterogeneous photocatalysis is less common but can provide unique avenues for inducing novel chemical transformations and can also be utilized for energy transductions, i.e., the energy in the photons can be captured in chemical bonds. Here, we developed a novel heterogeneous photocatalytic system that employs a lead-halide perovskite nanocrystal (NC) to capture photons and direct photogenerated holes to a surface bound transition metal Cu-site, resulting in a N-N heterocyclization reaction. The reaction starts from surface coordinated diamine substrates and requires two subsequent photo-oxidation events per reaction cycle. We establish a photocatalytic pathway that incorporates sequential inner sphere electron transfer events, photons absorbed by the NC generate holes that are sequentially funneled to the Cu-surface site to perform the reaction. The photocatalyst is readily prepared via a controlled cation-exchange reaction and provides new opportunities in photodriven heterogeneous catalysis.

CONVENIENT ROUTES TO ALKYL-SUBSTITUTED POLYAMINES

Alkyl-substituted polyamines, valuable for biological studies, can be prepared from N-phenylmethoxycarbonyl-1,4-diaminobutane (1b) and N-phenylmethoxycarbonyl-4-azidobutanamine (4a) by utilising the following reactions: (i) reduction of the phenylmethoxycarbonyl group to methyl by borane and (ii) combination of the Staudinger and aza-Wittig reactions .