86-86-2

Usage

Chemical Properties

white to cream powder

Uses

1-Naphthylacetamide (cas# 86-86-2) is a compound useful in organic synthesis.

Agricultural Uses

Plant growth regulator: 1-Naphthaleneacetamide is an agent for thinning fruit sets in apples and pear. Not currently registered for use in EU countries (pending). Registered for use in the U.S.

Trade name

AMACTONE?; AMID-THIN W?; FRUITONE?; ROOTONE? (component, with Indole-3-butyric acid and 1-Naphthaleneacetic acid); ROSETONE?; TRANSPLANTONE? (component, with 1-Naphthaleneacetic acid)

InChI:InChI=1/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14)

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 132-75-2 naphthalen-1-ylacetonitrile 
• 5121-00-6 naphthalen-1-yl-acetyl chloride 
• 90-15-3 α-naphthol 
• 79-07-2 Chloroacetamide 
• 26153-26-4 1-naphthylglyoxylic acid 
• 86-87-3 naphth-1-yl acetic acid 
• 352352-80-8 2-(naphthalen-1-yl)-2-oxoacetamide 

Downstream Products

• 86-87-3 naphth-1-yl acetic acid 
• 132-75-2 naphthalen-1-ylacetonitrile 
• 118-31-0 (naphth-1-yl)methylamine 
• 86-53-3 1-Cyanonaphthalene 
• 90-12-0 1-Methylnaphthalene 
• 2876-78-0 methyl 1-naphthylacetate 
• 78634-33-0 1-Phenyl-1,4-dihydro-3-(2H)benzoisoquinolinone 
• 110599-25-2 methyl N-1-naphtyl-p-tolylglycinate 
• 73867-08-0 α-(1-methyl-1-{[2-(1-naphthalenyl)ethyl]amino}-ethyl)benzenemethanol hydrochloride 
• 1235999-34-4 C₂₇H₁₉NO 
• 942-05-2 N-[2-(1-naphthyl)ethyl]amine hydrochloride 
• 50882-68-3 2-(naphthalen-1-yloxy)ethanamine 
• 4352-63-0 1H-naphtho[2,1-b]furan-2-one 
• 158833-27-3 N-benzyl-2-(naphthalen-1-yl)acetamide 

Relevant academic research and scientific papers

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Mechanochemical synthesis of primary amides from carboxylic acids using TCT/NH4SCN

A facile and effective approach toward the synthesis of primary amides from carboxylic acids has been developed. In the presence of 2,4,6-trichloro-1,3,5-triazine, a combination of ammonium thiocyanate and potassium carbonate led to the rapid conversion of carboxylic acids into the corresponding amides within five minutes grinding at room temperature. The use of ammonium thiocyanate as the amine source is unprecedented and exclusive formation of primary amides is observed only under the liquid-assisted grinding conditions.

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

PLANT GROWTH REGULATOR COMPRISING COMPOUND HAVING SUBSTITUENT COORDINATING TO ZINC

PROBLEM TO BE SOLVED: To provide a plant growth regulator having a more reduced risk of withering plants and to provide a simple plant growth regulating method. SOLUTION: Provided is a plant growth regulator that comprises, as an active ingredient, a compound or agriculturally acceptable salt, hydrate or solvate thereof in which the terminal carboxyl group in an indole or naphthalene compound having carboxy alkyl group is made to be a group or analog thereof derived from hydroxamic acid capable of coordinating to zinc. COPYRIGHT: (C)2015,JPOandINPIT

Pd(OAc)2-catalyzed lactonization of arylacetamides involving oxidation of C-H bonds

The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactones, the formation of which involves activation of the ortho C-H bonds, with concomitant cleavage of the directing group.

New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo

We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR. Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy) ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t1/2 ～ 3 h and CLint = 3.5 mL/min/kg, at 5 μM), and a low level of protein binding (25%, at 5 μM). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.