20030-70-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 4597, 1990 DOI: 10.1016/S0040-4039(00)97685-8

Upstream product

• 67-56-1 methanol 
• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 100-42-5 styrene 
• 6832-16-2 methyl diazoacetate 
• 186581-53-3 diazomethane 
• 103-26-4 Methyl cinnamate 
• 292638-85-8 acrylic acid methyl ester 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 17903-41-2 phenyl(trimethylsilyl)methyl bromide 
• 75-11-6 diiodomethane 
• 67074-44-6 trans-2-phenyl-1-cyclopropanecarbaldehyde 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 100-39-0 benzyl bromide 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 14814-55-2 2-phenylcyclopropane-1-carbohydrazide 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 33132-91-1 N,N-Dimethyl-2-phenyl-butylamin 
• 56434-66-3 1-Methyl-c-2-phenyl-r-1-cyclopropancarbonsaeure-methylester 
• 34271-31-3 trans-2-phenylcyclopropanecarbaldehyde 
• 110659-52-4 (1'R,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 110659-53-5 (+)-(1'R,2'S)-2-(2'-methylcyclopropyl)aniline 
• 29667-47-8 (+)-(1S,2R)-1-methyl-2-phenylcyclopropane 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 

Relevant academic research and scientific papers

Cp*Ru(II) and Cp*Ru(IV)-catalyzed reactions of CHX with vinyl C-H bonds: Competition between double bond homologation and olefin cyclopropanation by alkyl diazoacetate

When diazoesters are used as carbene precursors, new Ru(II) and Ru(IV) complexes bearing various substitutents tethered ligands mediate the formal carbene insertion into C-H vinyl bonds of (substituted) styrenes to yield mostly E- and Z-styrylacetic esters (e.g. 4-phenylbut-3-enoates with styrene). This rarely observed reaction competes with the cyclopropanation of the double bond. The influence of steric and electronic factors on the two competitive reactions is reported. The observation that the most efficient C-H insertion catalysts also promote the ROMP of norbornene lend support to the formation of ruthenacyclobutanes as reaction intermediates.

A fluorous phase approach to rhodium-catalyzed carbenoid reactions with diazoacetates

The cyclopropanation of alkenes with methyl diazoacetate in dichloromethane was catalyzed by rhodium(II) carboxylates containing a perfluoralkyl chain (Rh2L4, L = OOCC7F15 and OOC-C6H4-4-C

Boronic Acid-Mediated Photocatalysis Enables the Intramolecular Hydroacylation of Olefins Using Carboxylic Acids

An intramolecular hydroacylation of olefins using carboxylic acids (CAs) has been developed. With the aid of a boronic acid, CAs can be used as acyl-radical precursors in catalytic photoredox reactions driven by visible light. The CAs are easily converted into their corresponding cyclic ketones without the need to use any stoichiometric activating reagents. Mechanistic studies implied that the formation of an “ate” complex from the CA and boronic acid is crucial for the generation of the acyl radical equivalent from the unreactive carboxy group.

Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters

Diacids are important monomers in the polymer industry to construct valuable materials. Dicarboxylation of unsaturated bonds, such as alkenes and alkynes, with CO2 has been demonstrated as a promising synthetic method. However, dicarboxylation of C-C single bonds with CO2 has rarely been investigated. Herein we report a novel electrochemical ring-opening dicarboxylation of C-C single bonds in strained rings with CO2. Structurally diverse glutaric acid and adipic acid derivatives were synthesized from substituted cyclopropanes and cyclobutanes in moderate to high yields. In contrast to oxidative ring openings, this is also the first realization of an electroreductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggested that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of the products. Furthermore, we conducted polymerization of the corresponding diesters with diols to obtain a potential UV-shielding material with a self-healing function and a fluorine-containing polyester, whose performance tests showed promising applications.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

HETEROBICYCLIC CARBOXAMIDES AND USES THEREOF

Provided herein are heterobicyclic cyclopropanecarboxamide and heterobicyclic carboxamide compounds. In particular, provided herein are compounds that affect the function of kinases in a cell, and that are useful as therapeutic agents or with therapeutic agents. The compounds provided herein are useful in the treatment of a variety of diseases and conditions including eye diseases such as glaucoma, cardiovascular diseases, inflammatory diseases, and diseases characterized by abnormal growth, such as cancers. Also provided herein are compositions comprising heterobicyclic cyclopropanecarboxamide or heterobicyclic carboxamide compounds.

An efficient one-pot oxidative esterification of aldehydes to carboxylic esters using B(C6F5)3-TBHP

A simple and efficient protocol for oxidative esterification of diverse aldehydes with alcohols was accomplished with tert-butyl hydroperoxide and 1 mol % of tris(pentafluorophenyl)borane [B(C6F5)3] to generate the corresponding esters in good to excellent yields. The present protocol represents compatibility with wide range of functional groups as well as exceptional tolerance toward acid labile protecting groups such as TBDPS, TBDMS, acetonide, and Boc.

Synthesis of a novel C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) and its application as chiral ligand in asymmetric transition metal catalysis

The new C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) 2 with a chiral trans-(2R,3R)-2,3-bis(3,5-diphenylphenyl)cyclopropylidene (=trans-(2R,3R)-2,3-bis([1,1′: 3′,1″-terphenyl]-5′-yl) cyclopropylidene) backbone was efficiently synthesized (Scheme). All synthetic steps were easy to perform and led to the desired product in good overall yields. Compound 2 was tested and compared as ligand in several enantioselective catalytic reactions such as palladium(0)-catalyzed enantioselective allylic alkylations and copper(I)-catalyzed enantioselective cyclopropanations and aziridinations. Copyright

Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dimer. Further reaction leads to one or more trimers derived through two ene-reactions. The dimer formed easily undergoes cycloaddition

Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors

A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of 100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance in lean mice and diet induced obese mice.