Month: October 2022

In 2019,Organic Letters included an article by Tan, Jian-Ping; Yu, Peiyuan; Wu, Jia-Hong; Chen, Yuan; Pan, Jianke; Jiang, Chunhui; Ren, Xiaoyu; Zhang, Hong-Su; Wang, Tianli. Recommanded Product: 2-Hydroxy-4-methoxybenzaldehyde. The article was titled 《Bifunctional Phosphonium Salt Directed Enantioselective Formal [4 + 1] Annulation of Hydroxyl-Substituted para-Quinone Methides with α-Halogenated Ketones》. The information in the text is summarized as follows:

A highly diastereo- and enantioselective [4 + 1] cycloaddition of para-quinone methides to α-halogenated ketones was realized by bifunctional phosphonium salt catalysis, furnishing functionalized 2,3-dihydrobenzofurans in high yields and excellent stereoselectivities (>20:1 dr and up to >99.9% ee). Mechanistic observations suggested that the reaction underwent a cascade intermol. substitution/intramol. 1,6-addition process. DFT calculations revealed multiple H-bonding interactions between the catalyst and the enolate intermediate in the stereodetermining transition states. In addition to this study using 2-Hydroxy-4-methoxybenzaldehyde, there are many other studies that have used 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Recommanded Product: 2-Hydroxy-4-methoxybenzaldehyde) was used in this study.

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is employed in the synthesis of Schiff base ligand. It is applied as a reactant in the synthesis of LPA1R antagonists used in the inhibition of LPA-induced proliferation and contraction of normal human lung fibroblasts. Also used in the synthesis of tyrosine kinase 6 proteinase inhibitors.Recommanded Product: 2-Hydroxy-4-methoxybenzaldehyde

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2019,ChemistrySelect included an article by Mellado, Marco; Salas, Cristian O.; Uriarte, Eugenio; Vina, Dolores; Jara-Gutierrez, Carlos; Matos, Maria J.; Cuellar, Mauricio. Electric Literature of C8H8O2. The article was titled 《Design, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity》. The information in the text is summarized as follows:

The synthesis of seven new prenylated chalcones I (R = Ph, 2-HOC6H4, 4-MeOC6H4, etc.) obtained from the natural compound, 4-hydroxy-3-(3-methylbut-2-en-1-yl)acetophenone, previously isolated from S. graveolens, is reported. Five of these compounds exhibited high inhibition and selectivity against MAO-B with IC50 values in the low micromolar range. In addition, the antioxidant activity of this series was measured, with three compounds showing a better activity than the reference, butylated hydroxytoluene (BHT). Compound I (R = 4-Me2NC6H4) proved to be the best compound within the studied series (IC50 MAO-B = 8.19 μM and k DPPH = 3.73). Finally, mol. docking was performed to better understand the binding properties of these derivatives Important features for MAO-B inhibitory activity observed were hydrogen-bonding interaction between Tyr435 and nearness with Tyr398 and FAD co-factor. Therefore, these mols. were good candidates for the design of a lead compound for Parkinson’s disease. In addition to this study using 2-Methoxybenzaldehyde, there are many other studies that have used 2-Methoxybenzaldehyde(cas: 135-02-4Electric Literature of C8H8O2) was used in this study.

2-Methoxybenzaldehyde(cas: 135-02-4) is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. It also has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.Electric Literature of C8H8O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2019,Chemical Science included an article by Zhang, Yitao; Takale, Balaram S.; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H.. Category: ethers-buliding-blocks. The article was titled 《Sustainable ppm level palladium-catalyzed aminations in nanoreactors under mild, aqueous conditions》. The information in the text is summarized as follows:

A 1 : 1 Pd : ligand complex, [t-BuXPhos(Pd-Π-cinnamyl)]OTf, was identified as a highly robust pre-catalyst for amination reactions leading to diarylamines, where loadings of metal were typically at 1000 ppm Pd, run in water at temperatures between rt and 45 °C. The protocol was exceptionally simple, readily scaled and compared very favorably vs. traditional amination conditions. It was shown to successfully led to key intermediates associated with several physiol. active compounds In the part of experimental materials, we found many familiar compounds, such as 1-Bromo-3-methoxybenzene(cas: 2398-37-0Category: ethers-buliding-blocks)

1-Bromo-3-methoxybenzene(cas: 2398-37-0) can be used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The author of 《Base-Promoted Direct Chalcogenylation of 2-Naphthols》 were Lima, David B.; Santos, Pedro H. V.; Fiori, Priscila; Badshah, Gul; Luz, Eduardo Q.; Seckler, Diego; Rampon, Daniel S.. And the article was published in ChemistrySelect in 2019. Recommanded Product: 882-33-7 The author mentioned the following in the article:

An efficient and regioselective C1 chalcogenylation of 2-naphthol derivatives with a broad scope of diorganoyl dichalcogenides (S, Se) and lower amounts of the cheaper K2CO3 under atm. air in a short reaction time was developed to obtain organosulfur and organoselenium compounds I [R1 = H, 6-Br; R2 = Ph, 4-FC6H4, 4-MeOC6H4, etc.; R3 = S, Se; Z = CH, N]. The mechanistic studies indicated an ionic mechanism, essentially an electrophilic aromatic substitution, with a key role played by atm. oxygen for regeneration of the diorganoyl dichalcogenides.1,2-Diphenyldisulfane(cas: 882-33-7Recommanded Product: 882-33-7) was used in this study.

1,2-Diphenyldisulfane(cas: 882-33-7) belongs to ethers.Recommanded Product: 882-33-7Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The author of 《Phenanthrenone-based hole transport material for efficient dopant-free perovskite solar cells》 were Zou, Kaiyi; Gao, Peng; Ling, Xufeng; Song, Bo; Ding, Lei; Sun, Baoquan; Fan, Jian. And the article was published in Organic Electronics in 2019. Formula: C14H15NO2 The author mentioned the following in the article:

Spiro-OMeTAD is the most popular hole transport material (HTM) for perovskite solar cells. The insertion of one carbonyl group into the spirobifluorene framework in spiro-OMeTAD gave a novel phenanthrenone-based hole transport material (spiro-PT-OMeTAD). It is found that the introduction of one carbonyl group into spiro-PT-OMeTAD led to a big difference in the absorption behaviors, frontier MO energy levels and hole mobilities. The steady-state photoluminescence characterization and the space-charge-limited-current measurement indicate that this phenanthrenone-based material plays an important role in hole collection and transportation in perovskite solar cells. As a result, the dopant-free perovskite solar cells based on spiro-PT-OMeTAD showed highly improved performance by exhibiting a short-circuit c.d. of 22.36 mA/cm2, an open-circuit voltage of 0.99 V, and a fill factor of 0.62% under 1 sun illumination, which gave an overall power conversion efficiency (PCE) of 13.83%, compared to 10.5% for the spiro-OMeTAD based devices. The experimental process involved the reaction of Bis(4-methoxyphenyl)amine(cas: 101-70-2Formula: C14H15NO2)

Bis(4-methoxyphenyl)amine(cas: 101-70-2) is a diphenylamine derivative used as a chemical additive for cured rubber.Bis(4-methoxyphenyl)amine is highly toxic and may potentially induce chromosome abberation.Formula: C14H15NO2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The author of 《Modular Syntheses of Phenanthroindolizidine Natural Products》 were Jo, Young-In; Burke, Martin D.; Cheon, Cheol-Hong. And the article was published in Organic Letters in 2019. Application of 10365-98-7 The author mentioned the following in the article:

A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.3-Methoxyphenylboronic acid(cas: 10365-98-7Application of 10365-98-7) was used in this study.

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.Application of 10365-98-7

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes》 was published in Organic Letters in 2020. These research results belong to Yu, Wenqing; Liu, Long; Huang, Tianzeng; Zhou, Xiangbing; Chen, Tieqiao. Formula: C28H28O3 The article mentions the following:

A palladium-catalyzed decarbonylative alkenylation of aromatic carboxylic acids was developed. Under the reaction conditions, various benzoic acids including those bearing functional groups coupled to terminal alkenes, producing the corresponding internal alkenes in good to high yields. Cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalene, and febuxostat were also applicable to this reaction, demonstrating the potential synthetic value of this new reaction in organic synthesis. In the experiment, the researchers used many compounds, for example, 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid(cas: 106685-40-9Formula: C28H28O3)

6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid(cas:106685-40-9) may be used as a pharmaceutical reference standard for the quantification of the analyte in topical gel formulations using high-performance liquid chromatography technique.Formula: C28H28O3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《The Tetraethylphosphorodiamidate (OP(O)(NEt2)2) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement》 was published in Organic Letters in 2020. These research results belong to Alessi, Manlio; Patel, Jignesh J.; Zumbansen, Kristina; Snieckus, Victor. Application In Synthesis of m-Methoxyphenol The article mentions the following:

We report on the tetraethylphosphorodiamidate (-OP(O)(NEt2)2) group as an effective directed metalation group (DMG). Directed ortho-lithiation-electrophile quench of ArOP(O)(NEt2)2 (1a-e; Ar = substituted Ph, 2-naphthyl) provides a general synthesis of ortho-substituted aryl and naphthyl phosphorodiamidates. We also describe the phospha anionic ortho-Fries (AoF) rearrangement of the phosphorodiamidates 1a,b, giving phosphonates 3-R-2-[P(O)(NEt2)2]C6H3OH its vinylogous counterpart to the ortho-tolyl phosphorodiamidates. Intermol. competition experiments demonstrate the approx. equal DMG strength of the -OP(O)(NEt2)2 and the most powerful OCONEt2 groups. In the experiment, the researchers used m-Methoxyphenol(cas: 150-19-6Application In Synthesis of m-Methoxyphenol)

m-Methoxyphenol(cas: 150-19-6) may be used in synthesis of:C(4) symmetric calix[4]resorcinarene, 2-nitroso-5-methoxyphenol, 6-methoxy-2(3H)-benzoxazoloneApplication In Synthesis of m-Methoxyphenol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Open-Air Stereoselective Construction of C-Aryl Glycosides》 was published in Organic Letters in 2020. These research results belong to Lai, Mengnan; Othman, Karwan Abdulmajed; Yao, Hui; Wang, Qiuyuan; Feng, Yongkui; Huang, Nianyu; Liu, Mingguo; Zou, Kun. Safety of 3-Methoxyphenylboronic acid The article mentions the following:

A new methodol. of stereoselective C-glycosylation has been developed with 3,4-O-carbonate glycals and boronic acids, catalyzed by 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate under open-air conditions at room temperature This mild method is simple in operation, wide in substrate range, and tolerant in alc./phenolic hydroxyl and amino groups. High to excellent yields were observed for all substrates tested, with the driving force mainly contributed by decarboxylation. Meanwhile, the high 1,4-trans-selectivity was achieved by steric effects as proposed. The experimental part of the paper was very detailed, including the reaction process of 3-Methoxyphenylboronic acid(cas: 10365-98-7Safety of 3-Methoxyphenylboronic acid)

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.Safety of 3-Methoxyphenylboronic acid

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《D-p-D molecular semiconductors for perovskite solar cells: the superior role of helical versus planar p-linkers》 was written by Xu, Niansheng; Zheng, Aibin; Wei, Yuefang; Yuan, Yi; Zhang, Jing; Lei, Ming; Wang, Peng. Recommanded Product: Bis(4-methoxyphenyl)amine And the article was included in Chemical Science in 2020. The article conveys some information:

Controlling the mode of mol. packing and the size of mol. aggregates is of fundamental importance for high-performance charge transport materials in next-generation optoelectronic devices. To clarify the peculiar role of helicene as a kernel block in the exploration of unconventional organic semiconductors, in this work thia[5]helicene (T5H) is doubly aminated with electron-donating dimethoxydiphenylamine to afford T5H-OMeDPA, which is systematically compared with its perylothiophene (PET) congener (PET-OMeDPA). On the basis of the quantum theory of atoms in mols. and energy decomposition anal. of single crystals, it is surprisingly found that while p-p stacking of planar PET is stronger than that of helical T5H, this desirable effect for the charge transport of organic semiconductors is completely lost for donor-p-donor (D-p-D) type PET-OMeDPA but is retained for T5H-OMeDPA to a large extent. Consequently, the T5H-OMeDPA single-crystal presents about 5 times higher theor. hole-mobility than PET-OMeDPA. With respect to PET-OMeDPA, there is a weaker electronic coupling of helical T5H-OMeDPA with perovskites, leading to reduced interfacial charge recombination. Due to reduced transport resistance and enhanced recombination resistance, perovskite solar cells with T5H-OMeDPA exhibit a power conversion efficiency of 21.1%, higher than 19.8% with PET-OMeDPA and 20.6% with the spiro-OMeTAD control. In the experiment, the researchers used many compounds, for example, Bis(4-methoxyphenyl)amine(cas: 101-70-2Recommanded Product: Bis(4-methoxyphenyl)amine)

Bis(4-methoxyphenyl)amine(cas: 101-70-2) is a diphenylamine derivative used as a chemical additive for cured rubber.Bis(4-methoxyphenyl)amine is highly toxic and may potentially induce chromosome abberation.Recommanded Product: Bis(4-methoxyphenyl)amine

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem