Month: October 2022

COA of Formula: C14H21BO3On June 12, 2017, Zhu, Lei; Qi, Xiaotian; Li, Yingzi; Duan, Meng; Zou, Lufeng; Bai, Ruopeng; Lan, Yu published an article in Organometallics. The article was 《Ir(III)/Ir(V) or Ir(I)/Ir(III) Catalytic Cycle? Steric-Effect-Controlled Mechanism for the para-C-H Borylation of Arenes》. The article mentions the following:

A potential energy surface for iridium-catalyzed C-H-borylation of aromatic compounds was calculated; while bulky phosphine ligands favor Ir(I)-Ir(III) C-H activation, small amine ligands promote formation of triboryl Ir(V) intermediates. D. functional theory method N12 was used to study the mechanism of the [Ir(cod)OH]2/Xyl-MeO-BIPHEP-catalyzed para-selective C-H borylation reaction. The results revealed that the use of a bulky diphosphine ligand such as Xyl-MeO-BIPHEP was unfavorable for the previously proposed iridium(III)/iridium(V) catalytic cycle because it resulted in considerable steric repulsion in the hepta-coordinated iridium(V) intermediate. Inspired by this steric effect, we have proposed a novel iridium(I)/iridium(III)-based catalytic cycle for this transformation and shown that it can be used to account for the exptl. results. The iridium(I)/iridium(III) catalytic cycle induced by this steric effect consists of several steps, including: (i) the oxidative addition of the C-H bond of the substrate to an active iridium(I) boryl complex; (ii) the reductive elimination of a C-B bond; (iii) the oxidative addition of B2pin2 to an iridium(I) hydride complex; and (iv) the reductive elimination of a B-H bond. Notably, the computed regioselectivity of this reaction was consistent with the exptl. observations. The high para-selectivity of this reaction was also explained using structural anal. and a 2D contour model, which revealed that the strong steric repulsion between the diphosphine ligand and the meta-substituents resulted in a higher energy barrier for meta-C-H activation. The experimental process involved the reaction of 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1COA of Formula: C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. COA of Formula: C14H21BO3

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

The author of 《Recyclable nickel-catalyzed C-H/O-H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions》 were Tang, Zhi; Tong, Zhou; Xu, Zhihui; Au, Chak-Tong; Qiu, Renhua; Yin, Shuang-Feng. And the article was published in Green Chemistry in 2019. Reference of 2-Hydroxy-2-(4-propoxyphenyl)acetic acid The author mentioned the following in the article:

Herein, a protocol was developed for the efficient synthesis of 3-aryl-benzofuran-2(3H)-ones I [R = H, 5-Me, 7-t-Bu, etc.; R1 = Ph, 4-HOC6H4, 2-ClC6H4, etc.] via C-H/O-H bond dual functionalization of phenols with mandelic acids under solvent-free conditions using Ni(OTf)2 as catalyst. The nickel catalyst could be easily recycled in a test of three runs at the scale of 10 mmol without significant decline in the product yield. It was demonstrated that the yield of the desired products could be increased, for example, in the synthesis of the antioxidant Irganox HP-136 to a scale of 166 g. In the experimental materials used by the author, we found 2-Hydroxy-2-(4-propoxyphenyl)acetic acid(cas: 79694-16-9Reference of 2-Hydroxy-2-(4-propoxyphenyl)acetic acid)

2-Hydroxy-2-(4-propoxyphenyl)acetic acid(cas: 79694-16-9) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. Reference of 2-Hydroxy-2-(4-propoxyphenyl)acetic acid They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

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

In 2019,Organic Letters included an article by Yoo, Huen Ji; Youn, So Won. Recommanded Product: 673-22-3. The article was titled 《Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes》. The information in the text is summarized as follows:

Substituted coumarins and iminocoumarins were prepared regioselectively by cyclocondensation of ynamides (particularly N-alkynyl-N-methylmethanesulfonamides) with salicylaldehydes, o-hydroxyphenyl ketones, and o-aminophenyl ketones in the presence of ZnBr2. Generation of an ynamide in situ from 1-bromo-2-phenylethyne and N-methylmethanesulfonamide allowed the recycling of the methanesulfonamide through five cycles; the presence of coumarin did not inhibit the copper-catalyzed amination of the bromoalkyne. The experimental part of the paper was very detailed, including the reaction process of 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Recommanded Product: 673-22-3)

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: 673-22-3

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

In 2019,Organic Letters included an article by Chen, Yuye; Hu, Jingping; Guo, Lian-Dong; Tian, Peilin; Xu, Tianyue; Xu, Jing. Related Products of 60656-87-3. The article was titled 《Synthesis of the Core Structure of Daphnimacropodines》. The information in the text is summarized as follows:

Daphniphyllum alkaloids daphnimacropodines A-C possess a highly congested ring system and share a common tetracyclic ring skeleton. To access the challenging chem. structure of daphnimacropodines, a divergent synthetic approach toward their total synthesis is described. A stereoselective synthesis of the core structure I of daphnimacropodines has been achieved from a simple diketone building block. Our approach features an intramol. carbamate aza-Michael addition and a hydropyrrole synthesis via a Au-catalyzed alkyne hydration followed by an aldol condensation, whereas all the other attempts failed.2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Related Products of 60656-87-3) was used in this study.

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) may be used in the following syntheses: (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate ,(S)-5-benzyloxy-4-hydroxypentan-2-one, myxothiazols.Related Products of 60656-87-3

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

In 2019,ACS Energy Letters included an article by Ren, Ming; Wang, Jianan; Xie, Xinrui; Zhang, Jing; Wang, Peng. Safety of Bis(4-methoxyphenyl)amine. The article was titled 《Double-Helicene-Based Hole-Transporter for Perovskite Solar Cells with 22% Efficiency and Operation Durability》. The information in the text is summarized as follows:

Amelioration of the mobility and, in particular, the thermal stability of a hole-transporting mol. semiconductor is a practicable strategy to attain the enhancement of both power conversion efficiency (PCE) and operational durability of perovskite solar cells (PSCs). Here, a cost-effective double-[4]helicene-based mol. semiconductor (DBC-OMeDPA) is synthesized for a solution-deposited thin film, exhibiting an improved hole mobility in comparison with state-of-the-art spiro-OMeTAD control. X-ray crystallog. anal. and theor. calculation reveal the 3-dimensional mol. stacking and multidirectional hole-transporting property of DBC-OMeDPA, clarifying the microscopic mechanism of the hole-transport process. A better PCE of 22% at the AM 1.5G conditions is achieved for PSCs with DBC-OMeDPA as the hole-transporter. PSCs using DBC-OMeDPA characteristic of an elevated intrinsic glass transition temperature of 154° maintain a stable PCE output for hundreds of hours at 60° under equivalent full sunglight soaking.Bis(4-methoxyphenyl)amine(cas: 101-70-2Safety of Bis(4-methoxyphenyl)amine) was used in this study.

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.Safety of Bis(4-methoxyphenyl)amine

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

The author of 《Take Immune Cells Back on Track: Glycopolymer-Engineered Tumor Cells for Triggering Immune Response》 were Liu, Qi; Jiang, Shuaibing; Liu, Bing; Yu, You; Zhao, Zhen-Ao; Wang, Chao; Liu, Zhuang; Chen, Gaojian; Chen, Hong. And the article was published in ACS Macro Letters in 2019. Category: ethers-buliding-blocks The author mentioned the following in the article:

The “”self-homing”” of cancer cells to primary or metastatic tumor sites indicates that they could serve as vehicles for self-targeted cancer therapy; this suggests a promising method for treating end-stage cancer. Inspired by this, we propose that engineering cancer cells to carry efficient “”coup”” mols. for in situ activation of immune cells in or near tumor sites to attack tumors is a promising strategy for cancer therapy. Therefore, herein we explored the potential of engineered tumor cells to enhance their anticancer activity by stimulating immune cells. We armed tumor cell surfaces with specific glycopolymer-ligands that bind to lectins on macrophages or dendritic cells by combining HaloTag protein (HTP) fusion technique with reversible addition-fragmentation chain transfer (RAFT) polymerization We demonstrated that two synthetic well-defined glycopolymers containing, resp., N-acetylglucosamine and N-acetylmannosamine units, were introduced and stably presented on the cell surfaces via the stable covalent binding of chloroalkane-terminated polymers with membrane-bound HTP. Furthermore, it was shown that the glycopolymer-engineered HeLa cells with HTP anchors increased expression of the typical marker for M1-type macrophages (CD86) and upregulated secretion of pro-inflammatory cytokines (IL-12p70, TNF-α, and iNOS), thereby accelerating HeLa cell lysis. The maturation of dendritic cells was also promoted. This study demonstrates the strong potential of glycopolymer-engineered tumor cells in cancer immunotherapy. In the experimental materials used by the author, we found tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6Category: ethers-buliding-blocks)

tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Category: ethers-buliding-blocks

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

The author of 《Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl3 as the carbon monoxide-precursor》 were Xu, Fangning; Li, Dan; Han, Wei. And the article was published in Green Chemistry in 2019. Application of 529-28-2 The author mentioned the following in the article:

Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source was developed. The simple, efficient and environmentally benign method was successfully applied to the synthesis of fenofibric acid, naphthyl phenstatin and carbon-13 labeled biaryl ketone.1-Iodo-2-methoxybenzene(cas: 529-28-2Application of 529-28-2) was used in this study.

1-Iodo-2-methoxybenzene(cas: 529-28-2) participates in palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran in the presence of chiral ionic liquids containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations.Application of 529-28-2

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

The author of 《In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates》 were Xing, Linlin; Zhang, Yong; Li, Bing; Du, Yunfei. And the article was published in Organic Letters in 2019. Recommanded Product: 1,2-Diphenyldisulfane The author mentioned the following in the article:

The reaction of diorganyl disulfides or diselenides with PhICl2 in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramol. chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones, e.g., I and II, in good to excellent yields under metal-free conditions. In the experiment, the researchers used many compounds, for example, 1,2-Diphenyldisulfane(cas: 882-33-7Recommanded Product: 1,2-Diphenyldisulfane)

1,2-Diphenyldisulfane(cas: 882-33-7) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Recommanded Product: 1,2-Diphenyldisulfane

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

The author of 《Ortho/Ipso Alkylborylation of Aryl Iodides》 were Sui, Xianwei; Grigolo, Thiago A.; O’Connor, Colin J.; Smith, Joel M.. And the article was published in Organic Letters in 2019. Application In Synthesis of 1-Iodo-2-methoxybenzene The author mentioned the following in the article:

This work describes a method for the difunctionalization of aryl iodides to generate polysubstituted arenes via Pd catalysis. The reaction hinges on the unique interplay between norbornene and the metal catalyst to impart a guided ortho C-H alkylation event followed by a programmatic ipso borylation to provide a diverse array of substituted arene products. The utility of this transformation is demonstrated through the functionalization of the boronic ester to a variety of valuable functionalities. In the experiment, the researchers used many compounds, for example, 1-Iodo-2-methoxybenzene(cas: 529-28-2Application In Synthesis of 1-Iodo-2-methoxybenzene)

1-Iodo-2-methoxybenzene(cas: 529-28-2) participates in palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran in the presence of chiral ionic liquids containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations.Application In Synthesis of 1-Iodo-2-methoxybenzene

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

《Deuteration of Formyl Groups via a Catalytic Radical H/D Exchange Approach》 was published in ACS Catalysis in 2020. These research results belong to Zhang, Yueteng; Ji, Peng; Dong, Yue; Wei, Yongyi; Wang, Wei. Formula: C8H8O2 The article mentions the following:

H/D exchange at formyl groups represents the straightforward approach to C-1 deuterated aldehydes. This transformation has been recently realized by transition metal and NHC carbene catalysis. Mechanistically, all of these processes involve an ionic pathway. Herein, we report a distinct photoredox catalytic, visible light mediated neutral radical approach. Selective control of highly reactive acyl radical in the energy barrier surmountable, reversible reaction enables driving the formation of deuterated products when an excess of D2O is employed. The power of the H/D exchange process has been demonstrated for not only aromatic aldehydes but also aliphatic substrates, which have been difficult in transitional metal catalyzed H/D exchange reactions, and for selective late-stage deuterium incorporation into complex structures with uniformly high deuteration level (>90%). In the part of experimental materials, we found many familiar compounds, such as 2-Methoxybenzaldehyde(cas: 135-02-4Formula: C8H8O2)

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.Formula: C8H8O2

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