09/18/21 News The Shocking Revelation of C3H7NO2

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Identification of the C4 ‘-Oxidized Abasic Site as the Most Abundant 2-Deoxyribose Lesion in Radiation-Damaged DNA Using a Novel HPLC-Based Approach

A novel analytical high-performance liquid chromatography (HPLC)-based method of quantification of the yields of C4′-oxidized abasic sites, 1, in oxidatively damaged DNA has been elaborated. This new approach is based on efficient conversion of 1 into N-substituted 5-methylene-Delta(3)-pyrrolin-2-ones, 2, upon treatment of damaged DNA with primary amines in neutral or slightly acidic solutions with subsequent quantification of 2 by HPLC. The absolute and relative radiation-chemical yields of 1 in irradiated DNA solutions were re-evaluated using this method. The yields were compared with those of other 2-deoxyribose degradation products including 5-methylene-2(5H)-furanone, malondialdehyde, and furfural resulting from the C1′, C4′ and C5′-oxidations, respectively. The yield of free base release (FBR) determined in the same systems was employed as an internal measure of the total oxidative damage to the 2-deoxyribose moiety. Application of this technique identifies 1 as the most abundant sugar lesion in double-stranded (ds) DNA irradiated under air in solution (36% FBR). In single-stranded (ss) DNA this product is second by abundance (33% FBR) after 2-deoxyribonolactones (C1′-oxidation; 43% FBR). The production of nucleoside-5′-aldehydes (C5′-oxidation; 14% and 5% FBR in dsDNA and ssDNA, respectively) is in the third place. Taken together with the parallel reaction channel that converts C4′-radicals into malondialdehyde and 3′-phosphoglycolates, our results identify the C4’-oxidation as a prevalent pathway of oxidative damage to the sugar-phosphate backbone (50% or more of all 2-deoxyribose damages) in indirectly damaged DNA. (C) 2014 by Radiation Research Society

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

8 Sep 2021 News Our Top Choice Compound: C3H7NO2

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Acceptorless dehydrogenative coupling with Ru-based catalysts for the synthesis of N-heteroaromatic compounds

Ru-Catalyzed acceptorless dehydrogenative coupling (ADC) and auto-transfer-hydrogenative (ATH) reactions are effective, versatile transformations for the constructions of N-heteroaromatic compounds from alcohols. Water and hydrogen are the by-products and the starting alcohols are less toxic, more readily available and more easily handled than their halogenated counterparts. A variety of homogeneous ruthenium catalysts, alcohols and partner-substrates such as amines, ammonia, amidines and nitriles, have been used to build N-heteroaromatic compounds in one-pot, multi-step syntheses. This review details recently reported Ru catalysts employed for these reactions, describing the scope of each methodology, proposed reaction mechanisms, regioselectivity of coupling and applications in synthesis.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

06/9/2021 News The Absolute Best Science Experiment for C3H7NO2

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EPR free induction decay coherence observed after a single pulse in saturation recovery experiments for samples with resolved multiline CW spectra

An electron paramagnetic resonance (EPR) spin-coherence signal has been observed following a single pulse for rapidly tumbling radicals with well-resolved nuclear hyperfine splitting in fluid solution when B, is large enough to excite multiple hyperfine lines. This signal, which has the shape of a spin echo, arises from constructive interference of overlapping free induction decays (FIDs) from the hyperfine lines. It has been observed for 2,6-di-t-butyl-1,4-benzosemiquinone, 2,5-di-t-butyl-1,4-benzosemiquinone, 2,3,5,6-tetramethoxy-1,4-benzosemiquinone, 2,4,6-tri-t-butylphenoxyl radical, and 3carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy. It occurs at a time after the pulse that is equal to the inverse of the nuclear hyperfine splitting, independent of EPR resonance frequency from 250 MHz to 9.1 GHz. As the length of the pulse is increased, separate coherence signals can be observed that correspond to the beginning and end of the pulse. This coherence is distinct from the single-pulse echo signals discussed in the literature. For 2,6-di-t-butyl-1,4-benzosemiquinone, which has two resolved couplings (1.24 and 0.052 G), FID oscillations with a period that corresponds to the larger hyperfine coupling are observed on the coherence signal that arises from the smaller hyperfine coupling. If phase cycling is not perfect, the coherence signal can interfere with measurements of T-1 by saturation recovery.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

06/9/2021 News The Absolute Best Science Experiment for C3H7NO2

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EPR free induction decay coherence observed after a single pulse in saturation recovery experiments for samples with resolved multiline CW spectra

An electron paramagnetic resonance (EPR) spin-coherence signal has been observed following a single pulse for rapidly tumbling radicals with well-resolved nuclear hyperfine splitting in fluid solution when B, is large enough to excite multiple hyperfine lines. This signal, which has the shape of a spin echo, arises from constructive interference of overlapping free induction decays (FIDs) from the hyperfine lines. It has been observed for 2,6-di-t-butyl-1,4-benzosemiquinone, 2,5-di-t-butyl-1,4-benzosemiquinone, 2,3,5,6-tetramethoxy-1,4-benzosemiquinone, 2,4,6-tri-t-butylphenoxyl radical, and 3carbamoyl-2,2,5,5-tetramethyl-3-pyrrolin-1-yloxy. It occurs at a time after the pulse that is equal to the inverse of the nuclear hyperfine splitting, independent of EPR resonance frequency from 250 MHz to 9.1 GHz. As the length of the pulse is increased, separate coherence signals can be observed that correspond to the beginning and end of the pulse. This coherence is distinct from the single-pulse echo signals discussed in the literature. For 2,6-di-t-butyl-1,4-benzosemiquinone, which has two resolved couplings (1.24 and 0.052 G), FID oscillations with a period that corresponds to the larger hyperfine coupling are observed on the coherence signal that arises from the smaller hyperfine coupling. If phase cycling is not perfect, the coherence signal can interfere with measurements of T-1 by saturation recovery.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

03/9/2021 News The Shocking Revelation of C3H7NO2

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REACTION OF ACYLPYRUVATE ESTERS WITH A MIXTURE OF AROMATIC ALDEHYDE AND 1,3-DIAMINOPROPANE AND PHARMACOLOGICAL ACTIVITY OF THE PRODUCTS

1-(3-Aminopropyl)-5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones (I – X) were prepared via reaction of methyl acylpyruvates and a mixture of aromatic aldehyde and 1,3-diaminopropane in a 1: 1: 1 molar ratio. The products were converted to hydrochlorides XI – XV in 48 – 90% yields. 1,3-Di(4-acetyl-3-hydroxy-2-oxo-5phenyl- 3-pyrrolin-1-yl) propane (XVI) was produced in 16% yield via reaction of methyl acetylpyruvate with a mixture of benzaldehyde and 1,3-diaminopropane in a 2: 2: 1 molar ratio. The biological activity of the 12 products was studied.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

Sep 2021 News Can You Really Do Chemisty Experiments About C3H7NO2

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Transition-Metal-Free Cross-Coupling by Using Tertiary Benzylic Organoboronates

The transition-metal-free cross-coupling of alkyl or aryl electrophiles by using tertiary benzylic organoboronates is reported. This reaction involves the generation of tertiary alkyl anions from organoboronates in the presence of an alkoxide base and then their substitution reactions. This protocol allows the simple and efficient construction of quaternary carbon centers.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

1-Sep-2021 News Awesome Chemistry Experiments For C3H7NO2

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Photoactivated Refractive Index Anisotropy in Fluorescent Thiophene Derivatives

The optical control of anisotropy in materials is highly advantageous for many technological applications, including the real-time modulation of another light signal in photonic switches and sensors. Here, we introduce three thiophene derivatives with a donor-acceptor structure, which feature different positions of an electron-acceptor nitrile group, and both photoalignment and luminescence properties. Quantum chemical calculations highlight the presence of trans-forms stable at room temperature and metastable cis-isomers. Besides photoluminescence peaked at 440460 nm and 0.4 ns lifetime, the three nonlinear optical chromophores exhibit photoinduced anisotropy of the refractive index closely depending on the specific molecular structure, with higher values of birefringence at lower driving signal being obtained for ortho substitution of the nitrile group. All-optical modulation of an external light beam at rates of hundreds of hertz is demonstrated in the fluorescent systems. This finding opens an interesting route to multispectral photonic switches embedded in the active layers of light-emitting devices.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

Discover the magic of the Sarcosine

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Insights on the Pseudo-Enantiomeric Properties of Bifunctional Cinchona Alkaloid Squaramide-Derived Organocatalyst

The use of pseudo enantiomers is a well-known method of achieving products of complementary stereochemistry. Only rarely can different enantiomers of a product be accessed without modulation of the catalyst. Recently, a system was reported wherein two different enantiomers of spirocycles were obtained by a cascade reaction of unsaturated pyrrolin-4-ones with mercaptoacetaldehyde catalyzed by a single optimized cinchona alkaloid squaramide-derived organocatalyst. It was originally proposed that the E/Z geometry of the unsaturated pyrrolin-4-one dictated the stereochemistry of the spirocycle product, but this was not investigated further. In the present work, we have investigated the nature of a pseudo-enantiomeric organocatalyst conformation applying density functional theory calculations for investigating the transition states for the reaction. Furthermore, the influence of the double-bond geometry of the pyrrolin-4-one has been studied beyond what is possible to test experimentally. The results provide a greater understanding for this class of reactions that may be applicable in future methodology development.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

Chemical Properties and Facts of Sarcosine

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An aerobic and green C-H cyanation of terminal alkynes

This study describes a benign C-H cyanation of terminal alkynes with alpha-cyanoesters serving as a nontoxic cyanide source. In situ generation of the key copper cyanide intermediate is proposed by a sequence of alpha-C-H oxidation and copper-mediated beta-carbon elimination of alpha-cyanoesters, releasing the alpha-ketoester byproduct observed experimentally. The ensuing reaction of copper cyanide with terminal alkynes delivers preferentially cyanoalkynes and surpasses the possible Glaser type dimerization of terminal alkynes or the undesired accumulation of HCN under protic conditions. The presence of the co-oxidant K2S2O8 is crucial to this selectivity, probably by promoting oxidative transmetalation and the resulting formation of the Cu(iii)(acetylide)(CN) intermediate. All the reagents and salts used are commercially available, cheap and nontoxic, avoiding the use of highly toxic cyanide salts typically required in cyanation studies. The scope of this reaction is demonstrated with a set of alkynes and alpha-cyanoesters. The application of this method to late-stage functionalization of the terminal alkyne group in an estrone derivative is also feasible, showing its practical value for drug design.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

The Best Chemistry compound: Sarcosine

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PHOTOCYCLIZATION OF ALPHA,BETA-UNSATURATED AMIDE ALDEHYDES – SYNTHESIS OF JATROPHAM

alpha,beta-unsaturated amide aldehydes undergo photoisomerization and intramolecular cyclization to provide hydroxy substituted pyrrolidinone systems. A synthesis of the natural product jatropham was accomplished by application of this procedure.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem