68253-35-0

Usage

Uses

Used in Pharmaceutical Industry:
(E)-2,3-dihydro-1H-inden-1-one oxime is used as an intermediate in the synthesis of various pharmaceutical compounds due to its reactivity and ability to be incorporated into more complex molecular structures.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-2,3-dihydro-1H-inden-1-one oxime serves as a key component in the development of new agrochemical products, leveraging its properties to enhance the effectiveness of these compounds.
Used in Research Laboratories:
(E)-2,3-dihydro-1H-inden-1-one oxime is also utilized in research laboratories for its versatility in organic synthesis reactions, allowing scientists to explore new pathways and create novel compounds for various applications.
Handling and Storage:
Given its susceptibility to degradation, (E)-2,3-dihydro-1H-inden-1-one oxime is typically handled and stored under inert gas conditions to maintain its stability and ensure the integrity of the compound for its intended uses.

InChI:InChI=1/C9H9NO/c11-10-9-6-5-7-3-1-2-4-8(7)9/h1-4,11H,5-6H2/b10-9+

Upstream product

• 14548-38-0 6-chloro-1-indanone 
• 83-33-0 inden-1-one 
• 5470-11-1 hydroxylamine hydrochloride 
• 95-13-6 1-indene 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 78386-35-3 ethyl-(2-bromo-indan-1-yl)-ether 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 501-52-0 3-Phenylpropionic acid 
• 10368-44-2 trans-2-bromo-1-indanol 
• 19598-15-3 trans-1,2-bromoindane 
• 10485-09-3 2-bromoindene 
• 28873-89-4 2-Formylcinnamic acid 
• 681856-01-9 indan-1-one-O-(phenylmethyl)oxime 
• 496-11-7 INDANE 

Downstream Products

• 100485-57-2 Indan-1-one oxime 
• 83-33-0 inden-1-one 
• 98503-39-0 indanone-⁽¹⁾-[O-(toluene-sulfonyl-⁽⁴⁾)-seqtrans-oxime ] 
• 937371-85-2 (E)-indanone O-4-trifluoromethylbenzyl oxime 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 
• 214603-19-7 2,3-dihydro-1-oxo-1H-inden-2-yl-4-methylbenzenesulfonate 
• 10277-74-4 (S)-1-Aminoindane 
• 10277-74-4 (R)-1-Aminoindane 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 192461-80-6 N-[(1E)-2,3-dihydro-1H-inden-1-ylidene]-P,P-diphenylphosphinic amide 
• 98503-39-0 1-indanone-O-tosyloxime 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 681856-01-9 indan-1-one-O-(phenylmethyl)oxime 
• 154051-02-2 C₂₁H₁₈NOP 

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.

Photochemical Flow Oximation of Alkanes

The nitrosation of several alkanes using tert-butyl nitrite has been performed in flow showing a remarkable reduction in the reaction time compared with batch processing. Due to the necessity for large excesses of the alkane component a continuous recycling process was devised for the preparation of larger quantities of material.

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%.

Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex

Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.

PRODUCTION METHOD OF KETOXIME COMPOUND

PROBLEM TO BE SOLVED: To provide a new catalytic production method of a ketoxime that does not directly use hydroxyamine, nor require severe reaction conditions. SOLUTION: A production method of a ketoxime compound includes a step for transoximizing a ketone compound and ethyl acetohydroxamate in the presence of an organic solvent and a trifluoromethanesulfonic acid metal salt. The trifluoromethanesulfonic acid metal salt is preferably scandium (III) trifluoromethanesulfonate. The organic solvent is preferably methylene chloride, methanol, ethanol, n-propanol, or n-butanol. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

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.