14900-39-1 Usage
Description
1-Phenylvinylboronic acid is an organic compound that serves as a versatile reagent in various chemical reactions and synthetic processes. It is characterized by its boronic acid functional group, which allows it to participate in a range of coupling reactions, making it a valuable building block in organic synthesis.
Uses
Used in Pharmaceutical Industry:
1-Phenylvinylboronic acid is used as a synthetic intermediate for the preparation of enol esters, which are important in the halogenation of alkynes. This application is crucial for the development of new pharmaceutical compounds.
Used in Chemical Synthesis:
1-Phenylvinylboronic acid is used as a reactant in Liebeskind-Srogl cross-coupling, a method for the formation of carbon-carbon bonds. This reaction is essential for the synthesis of complex organic molecules, including those with potential applications in various industries.
Used in Material Science:
1-Phenylvinylboronic acid is used as a building block in the homocoupling of arylboronic acids, which leads to the synthesis of biaryls. Biaryls are important structural elements in many materials, such as liquid crystals and pharmaceuticals.
Used in Organic Synthesis:
1-Phenylvinylboronic acid is used as a component in the iterative cross-coupling of boronate building blocks. This process allows for the stepwise construction of complex molecular structures, which can be applied in various fields, including pharmaceuticals and agrochemicals.
Used in Enantioselective Synthesis:
1-Phenylvinylboronic acid is used as a reactant in enantioselective hydrogenation of hydroxyphenyl styrenes. This reaction is crucial for the synthesis of chiral compounds with specific optical properties, which are valuable in the pharmaceutical and agrochemical industries.
Used in Natural Product Synthesis:
1-Phenylvinylboronic acid is used as a reactant in samarium diiodide-mediated cyclization, which is employed for the synthesis of substituted benzannulated cyclooctanol derivatives. These compounds are found in various natural products and can be used as starting materials for the development of new drugs.
Used in Nucleoside Synthesis:
1-Phenylvinylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling, a method for the synthesis of C-6-substituted uridine phosphonates. These nucleoside analogs are important in the development of antiviral and anticancer drugs.
Check Digit Verification of cas no
The CAS Registry Mumber 14900-39-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,9,0 and 0 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14900-39:
(7*1)+(6*4)+(5*9)+(4*0)+(3*0)+(2*3)+(1*9)=91
91 % 10 = 1
So 14900-39-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H9BO2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-6,10-11H,1H2
14900-39-1Relevant articles and documents
The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes
Wang, Zhixin,Li, Yang,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
, p. 1810 - 1813 (2021/02/27)
In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.
Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols
Phipps, Erik J. T.,Rovis, Tomislav
supporting information, (2019/05/06)
We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.
Rhodium(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation
Phipps, Erik J. T.,Piou, Tiffany,Rovis, Tomislav
, p. 1787 - 1790 (2019/09/09)
We have developed a rhodium(III)-catalyzed cyclopropanation of unactivated olefins initiated by an alkenyl C-H activation. A variety of 1,1-disubstituted olefins undergo efficient cyclopropanation with a slight excess of alkene stoichiometry. A series of mechanistic interrogations implicate a metal carbene as an intermediate.
