5-Chlorodivaricatinic acid
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| Category | Others |
| Catalog number | BBF-05322 |
| CAS | |
| Molecular Weight | 244.67 |
| Molecular Formula | C11H13ClO4 |
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Description
5-Chlorodivaricatinic acid is a derivative of Divaricatinic acid. Divaricatinic acid is a metabolite isolated from the Andean lichens Protousnea poeppigii and Usnea florida displaying antimicrobial activity against the pathogenic fungi Microsporum gypseum, Trichophyton mentagrophytes and T. rubrum.
Specification
| Synonyms | 3-chloro-6-hydroxy-4-methoxy-2-propylbenzoic acid |
| IUPAC Name | 5-Chloro-2-hydroxy-4-methoxy-6-propylbenzoic acid |
| Canonical SMILES | CCCC1=C(C(=CC(=C1Cl)OC)O)C(=O)O |
| InChI | InChI=1S/C11H13ClO4/c1-3-4-6-9(11(14)15)7(13)5-8(16-2)10(6)12/h5,13H,3-4H2,1-2H3,(H,14,15) |
| InChI Key | JRBWSDAHJPBRDM-UHFFFAOYSA-N |
Reference Reading
1. Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid
James I Murray, Maria V Silva Elipe, Kyle D Baucom, Derek B Brown, Kyle Quasdorf, Seb Caille J Org Chem. 2022 Feb 18;87(4):1977-1985. doi: 10.1021/acs.joc.1c00886. Epub 2021 Jun 8.
The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ·NO2 radical is the active species.
2. Synthesis and Application of Constrained Amidoboronic Acids Using Amphoteric Boron-Containing Building Blocks
Harjeet S Soor, Diego B Diaz, Ka Yi Tsui, Karina Calvopiña, Marcin Bielinski, Dean J Tantillo, Christopher J Schofield, Andrei K Yudin J Org Chem. 2022 Jan 7;87(1):94-102. doi: 10.1021/acs.joc.1c02015. Epub 2021 Dec 13.
Amidoboronic acid-containing peptidomimetics are an important class of scaffolds in chemistry and drug discovery. Despite increasing interest in boron-based enzyme inhibitors, constrained amidoboronic acids have received little attention due to the limited options available for their synthesis. We describe a new methodology to prepare both α- and β-amidoboronic acids that impose restrictions on backbone angles. Lewis acid-promoted Boyer-Schmidt-Aube lactam ring expansions using an azidoalkylboronate enabled generation of constrained α-amidoboronic acid derivatives, whereas assembly of the homologous β-amidoboronic acids was achieved through a novel boronic acid-mediated lactamization process stemming from an α-boryl aldehyde. The results of quantum chemical calculations suggest carboxylate-boron coordination to be rate-limiting for small ring sizes, whereas the tetrahedral intermediate formation is rate limiting in the case of larger rings. As part of this study, an application of β-amidoboronic acid derivatives as novel VIM-2 metallo-β-lactamase inhibitors has been demonstrated.
3. Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Yi Chen, Di Liu, Rui Wang, Li Xu, Jingyao Tan, Mao Shu, Lingfeng Tian, Yuan Jin, Xiaoke Zhang, Zhihua Lin J Org Chem. 2022 Jan 7;87(1):351-362. doi: 10.1021/acs.joc.1c02385. Epub 2021 Dec 20.
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Brønsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
