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A simple method has been developed for the cross dehydrogenative coupling between two different primary alcohols using readily available RuCl2(PPh3)3 as a precatalyst through the borrowing-hydrogen approach. The present methodology is applicable to a large variety of alcohol derivatives including long chain aliphatic alcohols and heteroaryl alcohols. In addition, the methodology was applied in a straightforward protocol to synthesize commercially available fragrances such as Rosaphen and Cyclamenaldehyde in good yields.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A compound of the formula (I): and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, wherein: R2, R3, R4 and R5 are independently selected from the group consisting of H, C1-7 alkoxy, amino, halo or hydroxy; n is 1 or 2; RN1 and RN2 are independently selected from H and R, where R is optionally substituted C1-10 alkyl, C3-20 heterocyclyl and C5-20 aryl; or RN1 and RN2, together with the nitrogen atom to which they are attached form an optionally substituted 5-7 membered, nitrogen containing, heterocylic ring; Het is selected from: where Y1 and Y3 are independently selected from CH and N, Y2 is selected from CX and N and X is H, Cl or F; and where Q is O or S

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Microbial asymmetric reduction of ketone is an efficient tool for the synthesis of chiral alcohols. Many reports are available for the bio-reduction of acetophenone and its derivatives, since it is widely used model substrate. This research focus on exploring the soil fungal isolates for their ability towards the reduction of acetophenone and its derivatives to their corresponding chiral alcohols using growing cells instead of resting cells. Bio-reduction of acetophenone, 4-fluoro acetophenone, and 4-chloro acetophenone were carried out using different fungal cultures isolated from soil. All the isolates exhibited a good reduction capability when grown in an optimal condition. Among the screened fungal cultures, Penicillium sp. and Aspergillus sp. showed significant bioconversion with varying enantio-selectivity. However, the Penicillium sp. has showed maximum ability of bio-reduction. The best performing isolate was characterized using internal transcribed spacer (ITS) region and found to be Penicillium rubens VIT SS1, which showed higher conversion and selectivity more than 90% towards acetophenone and its derivatives. The reaction conditions such as pH, temperature and media were evaluated for the bio-reduction of acetophenone using Penicillium rubens VIT SS1. The substrate loading was increased from 0.5g/L to 6g/L at shake flask level using the optimized condition pH 5±0.5 and temperature 25±2C. This study revealed huge potential of fungal cultures for the synthesis of many aromatic chiral alcohols in a simpler, novel and cost effective manner.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Aryl chlorides in the presence of Pd/C catalyst and NaF react with primary alcohols to form esters, arenes, and alkanes. In this reaction, aryl chlorides act as both oxidants and coupling partners, whereas alcohols serve as both carbonyl sources and alkoxy components of the ester products. (Formula Presented).

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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3-Hydroxypyrimidine-2,4-dione (HPD) represents a versatile chemical core in the design of inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H and integrase strand transfer (INST). We report herein the design, synthesis and biological evaluation of an HPD subtype (4) featuring a cyclohexylmethyl group at the C-6 position. Antiviral testing showed that most analogues of 4 inhibited HIV-1 in the low nanomolar to submicromolar range, without cytotoxicity at concentrations up to 100 muM. Biochemically, these analogues dually inhibited both the polymerase (pol) and the RNase H functions of RT, but not INST. Co-crystal structure of 4a with RT revealed a nonnucleoside RT inhibitor (NNRTI) binding mode. Interestingly, chemotype 11, the synthetic precursor of 4 lacking the 3-OH group, did not inhibit RNase H while potently inhibiting pol. By virtue of the potent antiviral activity and biochemical RNase H inhibition, HPD subtype 4 could provide a viable platform for eventually achieving potent and selective RNase H inhibition through further medicinal chemistry.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The first asymmetric decarboxylative [4 + 3] annulation of propargylic carbamates with C,N-cyclic azomethine imines has been developed successfully by a copper-N-heterocyclic carbine system. This strategy led to a series of optically active isoquinoline-fused triazepine derivatives in good yields and with excellent enantio- and diastereoselectivities. Remarkably, Cu-allenylidene intermediates play a crucial role in this transformation.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The first manganese-catalyzed hydrogenation of esters to alcohols has been developed. The combination of Mn(CO)5Br with [HN(CH2CH2P(Et)2)2] leads to a mixture of cationic and neutral Mn PNP pincer complexes, which enable the reduction of various ester substrates, including aromatic and aliphatic esters as well as diesters and lactones. Notably, related pincer complexes with isopropyl or cyclohexyl substituents showed very low activity.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The design, synthesis, and structure-activity relationship of 3-oxybenzamides as potent inhibitors of the coagulation protease factor Xa are described on the basis of X-ray structures, privileged structure motifs, and SAR information. A total of six X-ray structures of fXa/inhibitor complexes led us to identify the major protein-ligand interactions. The binding mode is characterized by a lipophilic dichlorophenyl substituent interacting with Tyr228 in the protease S1 pocket, while polar parts are accommodated in S4. This alignment in combination with docking allowed derivation of 3D-QSAR models and tailored scoring functions to rationalize biological affinity and provide guidelines for optimization. The resulting models showed good correlation coefficients and predictions of external test sets. Furthermore, they correspond to binding site topologies in terms of steric, electrostatic, and hydrophobic complementarity. Two approaches to derive tailored scoring functions combining binding site and ligand information led to predictive models with acceptable predictions of the external set. Good correlations to experimental affinities were obtained for both AFMoC (adaptation of fields for molecular comparison) and the novel TScore function. The SAR information from 3D-QSAR and tailored scoring functions agrees with all experimental data and provides guidelines and reasonable activity estimations for novel fXa inhibitors.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Two compounds, obtained by random screening, and displaying micromolar activities on the mu opiate receptor were used as starting points for optimization. In that work, the traditional concept of the activity of a compound (related to one or a few targets) was extended to the comprehensive pharmacological profile of that compound on more than 70 receptors, transporters, and channels relevant to a CNS-oriented project. Using the two complementary design strategies based on two similarity concepts described in the previous paper, we have obtained analogues with IC50 values ranging between 0.9 nM and a few micromolar on the mu receptor and displaying qualitatively different profiles. We discuss here, both on a case-by-case basis and from a statistical standpoint, the pharmacological profiles in light of the two similarity concepts.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A combination of the abundant and low-cost triethylborane and sodium alkoxide generates a highly efficient catalyst for reduction of esters, as well as ketones and aldehydes, to alcohols using an inexpensive hydrosilane under mild conditions. The catalyst system exhibits excellent chemoselectivity and a high level of functional group tolerance. Mechanistic studies revealed a resting state of sodium triethylalkoxylborate that is the product of the reaction of BEt3 with sodium alkoxide. This borate species reacts with hydrosilane to form NaBEt3H, which rapidly reduces esters.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem