2'-O-Methylhyperphyllinic acid B

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2'-O-Methylhyperphyllinic acid B
Category Others
Catalog number BBF-05025
CAS 193816-31-8
Molecular Weight 570.67
Molecular Formula C32H42O9

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Description

2'-O-Methylhyperphyllinic acid B is a lichen depside.

Specification

Synonyms Benzoic acid, 2-hydroxy-4-methoxy-6-(2-oxoheptyl)-, 4-carboxy-3-methoxy-5-(2-oxononyl)phenyl ester; 4-Carboxy-3-methoxy-5-(2-oxononyl)phenyl 2-hydroxy-4-methoxy-6-(2-oxoheptyl)benzoate
IUPAC Name 4-((2-hydroxy-4-methoxy-6-(2-oxoheptyl)benzoyl)oxy)-2-methoxy-6-(2-oxononyl)benzoic acid

Properties

Boiling Point 709.8±60.0°C (Predicted)
Density 1.165±0.06 g/cm3 (Predicted)

Reference Reading

1. Total Syntheses of (±)-Dracocephalone A and (±)-Dracocequinones A and B
Taehwan Hwang, Joseph P Tuccinardi, Alexandra A Beard, Amy C Jackson, Min J Jung, John L Wood Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202210821. doi: 10.1002/anie.202210821. Epub 2022 Oct 17.
Described herein are the first total syntheses of (±)-dracocephalone A (1) and (±)-dracocequinones A (4) and B (5). The synthesis was initially envisioned as proceeding through an intramolecular isobenzofuran Diels-Alder reaction, a strategy that eventually evolved into a Lewis acid-promoted spirocyclization. This highly diastereoselective transformation set the stage for trans-decalin formation and a late-stage Suárez oxidation that produced a [3.2.1] oxabicycle suited for conversion to 1. Brønsted acid-mediated aromatization, followed by a series of carefully choreographed oxidations, allowed for rearrangement to a [2.2.2] oxabicycle poised for conversion to 4 and 5.
2. Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles
Lvnan Jin, Xuan Zhou, Yunbo Zhao, Jing Guo, Douglas W Stephan Org Biomol Chem. 2022 Oct 12;20(39):7781-7786. doi: 10.1039/d2ob01048h.
The control of chemoselective insertions of diazoalkanes into 2-hydroxybenzothiazoles is challenging. Herein, the chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles are achieved using B(C6F5)3, Rh2(OAc)4 or TfOH as the catalyst. This affords routes to 54 benzothiazole derivatives. These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Brønsted acid catalyses.
3. Lanthanoid-containing polyoxometalate nanocatalysts in the synthesis of bioactive isatin-based compounds
Mansoureh Daraie, Masoud Mirzaei, Maryam Bazargan, Vadjiheh Sadat Amiri, Bita Abdolahi Sanati, Majid M Heravi Sci Rep. 2022 Jul 14;12(1):12004. doi: 10.1038/s41598-022-16384-z.
Lanthanoid-containing polyoxometalates (Ln-POMs) have been developed as effective and robust catalysts due to their Lewis acid-base active sites including the oxygen-enriched surfaces of POM and the unique 4f. electron configuration of Ln. As an extension of our interest in Ln-POMs, a series of as-synthesized nanocatalysts K15[Ln(BW11O39)2] (Ln-B2W22, Ln = La, Ce, Nd, Sm, Gd, and Er) synthesized and fully characterized using different techniques. The Ln3+ ion with a big ionic radius was chosen as the Lewis acid center which is sandwiched by two mono-lacunary Keggin [BW11O39]9- units to form Ln-containing sandwiched type cluster. Consequently, the catalytic activity of nanocatalysts with different Ln was examined in the synthesis of bioactive isatin derivatives and compared under the same optimized reaction conditions in terms of yields of obtained products, indicating the superiority of the nano-Gd-B2W22 in the aforementioned simple one-pot reaction. The effects of different dosages of nanocatalyst, type of solvent, reaction time, and reaction temperature in this catalytic system were investigated and the best results were obtained in the presence of 10 mol% of nano-Gd-B2W22 in water for 12 min at the reflux condition.

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