Cyclopropylbenzene

Corbin, Thomas F.; Hahn, Roger C.; Shechter, Harold

doi:10.1002/0471264180.os044.10

Cited by 3 publications

(6 citation statements)

References 7 publications

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“…First, allylic bromination of 4-ethylbenzophenone 1 using N-bromosuccinimide (NBS) in CCl4 afforded the bromide derivative (R/S)-2 in 92 % yield (Scheme 2). 13 Then, the alkyl radical was generated in situ by the action of copper catalysts to the nitroxide (R/S)-3 14 with the bromide derivative yielded the alk 4 as a 4:1 mixture of diastereoisomers (55%). At this stage, the two diastereoisomers in racemic form were separated using column chromatography to afford 2.95 g of (RS/SR)-4 and 0.80 g of (RR/SS)-4.…”

Section: Resultsmentioning

confidence: 99%

“…First, allylic bromination of 4-ethylbenzophenone 1 using N -bromosuccinimide (NBS) in CCl 4 afforded the bromide derivative ( R / S )- 2 in 92% yield (Scheme ). Then, the alkyl radical was generated in situ by the reaction of copper catalysts with the nitroxide ( R / S )- 3 with the bromide derivative yielding the Alk 4 as a 4:1 mixture of diastereoisomers (55%).…”

Section: Resultsmentioning

confidence: 99%

“…1 H, 13 C, and 31 P NMR spectra of 2, (RR/SS)-4, (RS/SR)-4, (RS/ SR)-5, and (RS/SR)-6 were recorded in CDCl 3 on a 300 or 400 MHz spectrometer at Marseille and 1 H, correlation spectroscopy (COSY), and total correlation spectroscopy (TOCSY) NMR spectra of 9, 12, and 13 were recorded in the DMSO-d 6 solvent at room temperature (T = 298 K) on a BRUKER AVANCE spectrometer at 300 MHz at Nancy. Chemical shifts (δ) are given in parts per million (ppm) and for obtaining the 1 H and 13 C NMR spectra, residual nondeuterated solvents were used as the internal reference, an internal capillary filled with 85% H 3 PO 4 was used for obtaining the 31 P NMR spectra of 2, (RR/SS)-4, (RS/SR)-4, (RS/SR)-5, and (RS/SR)-6, and the DMSO residual peak (δ = 2.5 ppm) was used as the internal reference for 9, 12, and 13.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Design of a Targeting and Oxygen-Independent Platform to Improve Photodynamic Therapy: A Proof of Concept

Larue

Koumba

Breton

et al. 2021

ACS Appl. Bio Mater.

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Photodynamic therapy (PDT) is a promising technique to treat different kinds of disease especially cancer. PDT requires three elements: molecular oxygen, a photo-activatable molecule called the photosensitizer (PS) and appropriate light. Under illumination, the PSs generate, in the presence of oxygen, the formation of reactive oxygen species including singlet oxygen, toxic, which then destroys the surrounding tissues. Even if PDT is used with success to treat actinic keratosis or prostate cancer for example, PDT suffers from two major drawbacks: the lack of selectivity of most of the PSs currently used clinically as well as the need for oxygen to be effective. To remedy the lack of selectivity, targeting the tumor neovessels is a promising approach to destroy the vascularization and cause asphyxia of the tumor. KDPPR peptide affinity for the NRP-1 receptor overexpressed on endothelial cells has already been proven. To compensate for the lack of oxygen, we focused on photoactivatable alkoxyamines, molecules capable of generating toxic radicals by light activation. In this paper we describe the synthesis of a multifunctional platform combining three units: a PS for an oxygen-dependent PDT, a peptide to target tumor neovessels and an alkoxyamine for an oxygen-independent activity. The synthesis of the compound was successfully carried out, the study of the photophysical properties showed that the PS retained its capacity to form singlet oxygen, the affinity tests confirmed the affinity of the compound for NRP-1. Thanks to the Electron Paramagnetic Resonance (EPR) spectroscopy, a technique of choice for radical investigation, the radicals generated by the illumination of the alkoxyamine could be detected. The proof of concept was thus successfully established.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Design of a Targeting and Oxygen-Independent Platform to Improve Photodynamic Therapy: A Proof of Concept

Larue

Koumba

Breton

et al. 2021

ACS Appl. Bio Mater.

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“…All reagents, with the exceptions of diethyl cinnamylmalonate 20 and 1,3-dibromo-1-phenylpropane, 29 were purchased from the Aldrich Chemical Co. (Milwaukee, WI) and used without further purification. Solvents were dried, when necessary, by standard methods.…”

Section: Generalmentioning

confidence: 99%

Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

Lasa

López

Cativiela

2005

Tetrahedron: Asymmetry

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Cyclopropylbenzene

Abstract: Cyclopropylbenzene intermediate: 1,3‐dibromo‐1‐phenylpropane product: cyclopropylbenzene

Cited by 3 publications

References 7 publications

Design of a Targeting and Oxygen-Independent Platform to Improve Photodynamic Therapy: A Proof of Concept

Design of a Targeting and Oxygen-Independent Platform to Improve Photodynamic Therapy: A Proof of Concept

Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

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