276888-00-7

Basic information

• Product Name: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate
• Synonyms: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate
• CAS NO: 276888-00-7
• Molecular Formula: C13H15O4
• Molecular Weight: 235.2558
• Mol File: 276888-00-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(276888-00-7)
• EPA Substance Registry System: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(276888-00-7)

Safety Data

• Hazardous Substances Data: 276888-00-7(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Industry:
2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate is used as a flavoring ingredient in food products for its ability to impart a distinct and pleasant taste, enhancing the overall sensory experience of the product.
Used in Fragrance Industry:
In the perfume and cosmetics sector, 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate serves as a fragrance ingredient, leveraging its fruity scent to create appealing and long-lasting aromas in various personal care products.
Used in Chemical Synthesis:
2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate is utilized in the synthesis of other organic compounds, acting as a key intermediate in the production of various chemical products, thus contributing to the diversity of chemical compounds available for different applications.
Used as a Reagent in Chemical Reactions:
DMDIDC also functions as a reagent in chemical reactions, facilitating specific transformations and processes that are essential in the development of new chemical entities and materials.
While DMDIDC is not considered highly toxic, it is important to handle and store it with care to prevent potential irritation and adverse effects, ensuring safety in its applications across various industries.

Upstream product

• 63104-44-9 dimethyl 2,2-di(prop-2-ynyl)malonate 
• 74-86-2 acetylene 
• 91-13-4 α,α'-dibromo-o-xylene 
• 108-59-8 malonic acid dimethyl ester 
• 81395-28-0 1-((benzyloxy)methyl)-2-bromobenzene 
• 119367-65-6 2-<(Benzyloxy)methyl>benzaldehyde 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 873402-73-4 2-ethoxymethyl-benzaldehyde 
• 80171-34-2 1-bromo-2-(ethoxymethyl)benzene 

Downstream Products

• 68499-29-6 bistosylate of 2,2-bis(hydroxymethyl)-indan 

Relevant articles and documents

Ruthenium(II)-catalyzed selective intramolecular [2 + 2 + 2] alkyne cyclotrimerizations

In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes chemoselectively reacted with monoalkynes at ambient temperature to afford the desired bicyclic benzene derivatives in good yields. A wide variety of diynes and monoynes containing functional groups such as ester, ketone, nitrile, amine, alcohol, sulfide, etc. can be used for the present ruthenium catalysis. The most significant advantage of this protocol is that the cycloaddition of unsymmetrical 1,6-diynes with one internal alkyne moiety regioselectively gave rise to meta-substituted products with excellent regioselectivity. Completely intramolecular alkyne cyclotrimerization was also accomplished using triyne substrates to obtain tricyclic aromatic compounds fused with 5-7-membered rings. A ruthenabicycle complex relevant to these cyclotrimerizations was synthesized from Cp*RuCl(cod) and a 1,6-diyne possessing phenyl terminal groups, and its structure was unambiguously determined by X-ray analysis. The intermediary of such a ruthenacycle intermediate was further confirmed by its reaction with acetylene, giving rise to the expected cycloadduct. The density functional study on the cyclotrimerization mechanism elucidated that the cyclotrimerization proceeds via oxidative cyclization, producing a ruthenacycle intermediate and subsequent alkyne insertion initiated by the formal [2 + 2] cycloaddition of the resultant ruthenacycle with an alkyne.

Highly chemo- and regio-selective [2 + 2 + 2] cycloaddition of unsymmetrical 1,6-diynes with terminal alkynes catalyzed by Cp*Ru(cod)Cl under mild conditions

Ru(n)-catalyzed cycloaddition of unsymmetrical 1,6-diynes gives the desired cycloadducts in high yields with a regioselectivity meta:ortho = 88:12-98:2.

Divergent Access to Seven/Five-Membered Rings Based on [1,6]-Hydride Shift/Cyclization Process

We have achieved a divergent access to seven/five-membered rings based on a [1,6]-hydride shift/cyclization process from benzylidenemalonate with an o-alkoxymethyl group. Whereas Yb(OTf)3 afforded benzoxepines (with a seven-membered ring) selectively, indanes (with a five-membered ring) were the main products when Sc(OTf)3 was employed.

Potential antidepressants displayed combined α2-adrenoceptor antagonist and monoamine uptake inhibitor properties

Classical antidepressants are thought to act by raising monoamine (serotonin and noradrenaline) levels in the brain. This action is generally accomplished either by inhibition of monoamine metabolism (MAO inhibitors) or by blockade of monoamine uptake (tricyclic antidepressants and selective serotonin or noradrenaline reuptake inhibitors). However, all such agents suffer from a time lag (3-6 weeks) before robust clinical efficacy can be demonstrated. This delay may reflect inhibitory actions of noradrenaline at presynaptic α2A-adrenergic auto- or heteroreceptors which gradually down-regulate upon prolonged exposure. Blockade of presynaptic α2A-adrenoceptors by an antagonist endowed with monoamine uptake inhibition properties could lead to new antidepressants with greater efficacy and a shorter time lag. In the literature, only two molecules-have been described with such a pharmacological profile. Of these, napamezole (2) was chosen as a point of departure for the design of 4(5)-[(3,4-dihydro-2-naphthalenyl)methyl]-4,5-dihydroimidazole (4a), which displayed the desired profile: α2A-adrenoceptor antagonist properties and serotonin/noradrenaline uptake inhibition. From this original molecule, a series of derivatives was designed and synthesized, encompassing substituted as well as rigid analogues. Structure-activity relationships permitted the selection of 14c (4(5)-[(5-fluoroindan-2-yl)methyl]-4,5-dihydroimidazole) as a development candidate.