71778-34-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,2R)-ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique cyclopropane ring and chiral center provide opportunities for the development of novel drugs with specific biological activities.
Used in Organic Chemistry Research:
In the field of organic chemistry, (1R,2R)-ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate serves as an intriguing subject for research. Its reactivity and the influence of the cyclopropane ring on its biological activity make it a promising candidate for exploring new reaction pathways and mechanisms.
Used in Drug Development:
(1R,2R)-ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate is employed as a precursor in drug development, potentially leading to the creation of new therapeutic agents. Its structural features may offer advantages in terms of selectivity, potency, and pharmacokinetics, which are crucial for effective drug design.
Used in Medicinal Chemistry:
In medicinal chemistry, (1R,2R)-ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate is used as a building block for the design and synthesis of bioactive molecules. Its unique structural elements can be leveraged to create compounds with specific pharmacological targets and therapeutic applications.
Overall, (1R,2R)-ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate's diverse applications across various scientific disciplines highlight its potential as a versatile and valuable compound in the fields of pharmaceuticals, organic chemistry, and drug development.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 626-20-0 3-methoxystyrene 
• 591-31-1 3-methoxy-benzaldehyde 
• 33877-04-2 ethyl (E)-3-(3-methoxyphenyl)acrylate 
• 36501-44-7 (Diethylamino)dimethyloxosulfonium tetrafluoroborate 
• 766-85-8 3-methoxy-1-iodobenzene 
• 64-17-5 ethanol 
• 6099-04-3 trans-3-methoxycinnamic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 96728-38-0 trans-[2-(3-methoxyphenyl)cyclopropane]carboxylic acid 
• 71104-74-0 trans-<2-(m-methoxyphenyl)cyclopropyl>methyl acetate 
• 71104-74-0 cis-<2-(m-methoxyphenyl)cyclopropyl>methyl acetate 
• 114095-60-2 (trans-2-(3-methoxyphenyl)cyclopropyl)methanol 

Relevant academic research and scientific papers

Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives

In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Br?nsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway.

Asymmetric, Nearly Barrierless C(sp3)-H Activation Promoted by Easily-Accessible N-Protected Aminosulfoxides as New Chiral Ligands

Although chiral sulfoxides are important motifs in medicinal chemistry and asymmetric synthesis, design and applications of sulfoxide ligands are still limited, in particular in the context of asymmetric C-H activation. We disclose herein the conception a

Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides

The in situ reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.

One-pot approach for the synthesis of trans-cyclopropyl compounds from aldehydes. Application to the synthesis of GPR40 receptor agonists

A novel multicatalytic one-pot process providing trans-cyclopropyl compounds from corresponding aldehydes has been developed and applied to the synthesis of GPR40 small molecule agonists. The Royal Society of Chemistry.

Solvolysis of 1-[trans-2-(m- Orp-Substituted Phenyl)cyclopropyl]- 1-methylethyl p-Nitrobenzoates

The solvolyses of 1-[trans-2-(m- or p-substituted phenyl)cyclopropyl]-1-methylethyl p-nitrobenzoates in 80% aqueous acetone have been studied with regard to both reactivity and product composition. For the less reactive substituents such as m-Br, m-Cl, and m-CF3, the solvolysis products were the corresponding 2-(2-arylcyclopropyl)-2-propanol, indicating the cyclopropylmethyl cation intermediate. The ring-opened products increased as the electron-donating ability of the substituents increased. The application of the Yukawa-Tsuno equation to the reactivity afforded a ρ value of -1.43 and r value of 0.59 with a correlation coefficient of 0.997. A large value of r indicates the presence of the allylic cation intermediate where much more charge develops at the benzylic carbon for the derivatives with electron-donating substituents than is the case for the cyclopropylmethyl cation intermediate. Thus the solvolysis reaction proceeds via two independent pathways: one has a cyclopropyl cation intermediate and the other has a homoallylic cation intermediate.

ARYLCYCLOPROPANE PHOTOCHEMISTRY. UNUSUAL AROMATIC SUBSTITUENT EFFECTS ON THE PHOTOCHEMICAL REARRANGEMENT OF (2-ARYLCYCLOPROPYL)METHYL ACETATES TO 1-ARYLHOMOALLYL ACETATES.

Irradiation of trans(2-arylcyclopropyl)methyl acetates a 4-butenyl-1-arylacetate (7a,b,d-h) via an ionic mechanism from the singlet state. Similar rearrangements occurred with exo-(1,1a,6,6a-tetrahydrocycloprop left bracket a right bracket inden-1-yl)methyl acetate and the 4-cyano derivative. Excited state reaction rate constants were determined from reactant fluorescence lifetimes and product quantum yields. It is concluded that the rate-determining step involves conversion of the initially formed aromatic excited state to a reactive cyclopropane excited state and that cyclopropane to aromatic ring charge transfer enhances this process.