3349-60-8

Usage

Uses

Used in Organic Synthesis:
1-Indanone oxime is used as a reagent in organic synthesis for the preparation of various nitrogen-containing compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
1-Indanone oxime is used as a research compound in pharmaceutical research for its potential applications in the treatment of neurological disorders. It has been studied for its ability to inhibit the enzyme monoamine oxidase, which plays a crucial role in the regulation of neurotransmitters in the brain.
Used in Antimicrobial Applications:
1-Indanone oxime is used as an antimicrobial agent in the development of pharmaceuticals. Its antimicrobial properties have been investigated for potential use in treating infections caused by various microorganisms.

InChI:InChI=1/C9H9NO/c11-10-9-6-5-7-3-1-2-4-8(7)9/h1-4,11H,5-6H2

Upstream product

• 83-33-0 inden-1-one 
• 19598-15-3 trans-1,2-bromoindane 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 501-52-0 3-Phenylpropionic acid 
• 10368-44-2 trans-2-bromo-1-indanol 
• 78386-35-3 ethyl-(2-bromo-indan-1-yl)-ether 
• 10485-09-3 2-bromoindene 
• 28873-89-4 2-Formylcinnamic acid 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 681856-01-9 indan-1-one-O-(phenylmethyl)oxime 
• 95-13-6 1-indene 

Downstream Products

• 192461-80-6 N-[(1E)-2,3-dihydro-1H-inden-1-ylidene]-P,P-diphenylphosphinic amide 
• 681856-01-9 indan-1-one-O-(phenylmethyl)oxime 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 40358-33-6 2,3,4,5-tetrahydro-benzo[b][1,4]thiazepine 
• 1236106-50-5 (4-methoxyphenyl)(1-thioxo-1H-inden-2-yl)phosphinodithioic acid 
• 1236106-51-6 phenyl hydrogen (1-thioxo-1H-inden-2-yl)-phosphonotrithioate 
• 860746-62-9 N-((1S,3aR,7aR)-octahydro-1H-inden-1-yl)acetamide 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 

Relevant academic research and scientific papers

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis

Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate the use of a single rhodium precursor that acts in both the homogeneous and heterogeneous phases for the asymmetric full saturation of vinylarenes that, to date, constitute an unmet bottleneck in the field. A simple asymmetric hydrogenation of a styrenic olefin, enabled by a ligand accelerated effect, accounted for the facial selectivity in the consecutive arene hydrogenation. Tuning the ratio between the phosphine ligand and the rhodium precursor controlled the formation of homogeneous and heterogeneous catalytic species that operate without interference from each other. The system is flexible in terms of both the chiral ligand and the nature of the external olefin. We anticipate that our findings will promote the development of asymmetric arene hydrogenations.

Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides

We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.

Deconstructive Oxygenation of Unstrained Cycloalkanamines

A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto-oxidative aromatization promoted C(sp3)?C(sp3) bond cleavage strategy. This metal-free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto-oxidative annulation to in situ generate pre-aromatics, followed by N-radical-promoted ring-opening and further oxygenation by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and m-cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4-triazole-containing acyclic carbonyl compounds were efficiently produced. This protocol features a one-pot operation, mild reaction conditions, high regioselectivity and ring-opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids.

Access to Cyanoimines Enabled by Dual Photoredox/Copper-Catalyzed Cyanation of O-Acyl Oximes

An efficient strategy for the synthesis of pharmaceutically important and synthetically useful cyanoimines, as well as cyanamides, has been described. This strategy is enabled by dual photoredox/copper-catalyzed cyanation of O-acyl oximes or O-acyl hydroxamides. This state of the art protocol for cyanoimines and cyanamides features readily available starting materials, mild reaction conditions, good functional group tolerance, and operational simplicity. The resultant cyanoimines can be transformed into structurally diverse and functionally important N-containing heterocycles.

Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock

Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The total synthesis of this intermediate is based on the utilization of naphthalene as a readily accessible, economically attractive, and thus favorable petrochemical starting material. At first, naphthalene is transformed into 4-carboxy-indanone within a four-step process by means of an initial Birch reduction, followed by an isomerization of the C=C double bond, oxidative C=C cleavage, and intramolecular Friedel-Crafts acylation. The transformation of the 4-carboxy-indanone into (S)-4-cyano-1-aminoindane then represents the key step for introducing the chirality and the desired absolute S configuration. When evaluating complementary biocatalytic approaches based on the use of a lipase and transaminase, respectively, the combination of a chemical reductive amination of the 4-carboxyindanone followed by a subsequent lipase-catalyzed resolution turned out to be the most efficient route, leading to the desired key intermediate (S)-4-cyano-1-aminoindane in satisfactory yield and with excellent enantiomeric excess of 99%.

PROCESS AND INTERMEDIATES FOR THE RACEMIZATION OF ENANTIOMERICALLY ENRICHED 1-AMINOINDANE

The present invention relates to an improved process for the racemization of (S) -1-aminoindane. (S) -1-aminoindane is formed as a side product in the process of preparation (R) -1-aminoindane by enantiomeric resolution of racemic 1-aminoindane. (R) -aminoindane is a valuable intermediate in the process of preparation of rasagiline.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes

A series of zinc acetate complexes with optically pure diphenylethanediamine (DPEDA)-derived ligands have been employed as enantioselective catalyst for the hydrosilylation of various imines. High control of stereoselectivity (up to 97% ee) and excellent yields (up to 96%) were gained for a broad range of N-phosphinoylimines by using (R,R)-N,N′-dibenzyl-1,2-diphenylethane-1,2-diamine. This is the first successful application of an air-stable and environmentally friendly chiral Zn(OAc)2 complex instead of the previously used harmful diethylzinc in the asymmetric reduction of the C=N double bond.

TETRAZOLINONE COMPOUND AND USE THEREOF

The compound represented by formula (1): wherein R4 and R5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R7, R8, and R9 each represents a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group, or the like; R13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.