![molecular formula C31H49O2P B580627 Di-tert-butil(2',4',6'-triisopropil-3,6-dimetoxi-[1,1'-bifenil]-2-il)fosfina CAS No. 1160861-53-9](/img/structure/B580627.png)
Di-tert-butil(2',4',6'-triisopropil-3,6-dimetoxi-[1,1'-bifenil]-2-il)fosfina
Descripción general
Descripción
TBuBrettPhos, also known as TBuBrettPhos, is a useful research compound. Its molecular formula is C31H49O2P and its molecular weight is 484.705. The purity is usually 95%.
BenchChem offers high-quality tBuBrettPhos suitable for many research applications. Different packaging options are available to accommodate customers' requirements. Please inquire for more information about tBuBrettPhos including the price, delivery time, and more detailed information at [email protected].
Aplicaciones Científicas De Investigación
N-Arilación de ésteres de aminoácidos
tBuBrettPhos se ha utilizado como precatalizador para la N-arilación de ésteres de aminoácidos utilizando triflato de arilo. Cabe destacar que esta reacción se produce en condiciones suaves, lo que minimiza la racemización del éster de aminoácido. La capacidad de introducir selectivamente grupos arilo en derivados de aminoácidos es valiosa en química medicinal y síntesis de péptidos .
Conversión de haluros de arilo a fenoles
En presencia de benzaldoxima como sustituto del hidróxido, tBuBrettPhos cataliza la conversión de haluros de arilo (como cloruros y bromuros de arilo) a fenoles. Esta transformación proporciona una ruta directa a los compuestos fenólicos, que tienen aplicaciones en productos farmacéuticos, agroquímicos y ciencia de los materiales .
Formación de enlaces C-C, C-N y C-O
tBuBrettPhos es muy versátil en la formación de diversos enlaces mediante reacciones de acoplamiento cruzado catalizadas por paladio:
- Formación de enlaces C-O: Promueve la arilación de alcoholes, fenoles y otros sustratos que contienen oxígeno, obteniendo productos valiosos .
Estabilidad y solubilidad
- Solubilidad: Se disuelve bien en una amplia gama de disolventes orgánicos, lo que mejora su aplicabilidad en diversas condiciones de reacción .
Otros precatalizadores de Buchwald
Si bien tBuBrettPhos es un jugador estrella, mencionemos brevemente un par de precatalizadores relacionados:
- tBuXPhos: Otro ligando de Buchwald, tBuXPhos, mejora la formación de enlaces C-O y C-N catalizados por Pd. Encuentra aplicaciones en sustituciones de Tsuji-Trost, acoplamiento cruzado de fluoruros bencílicos y reacciones de acoplamiento C-N con sulfinamidas y haluros de arilo .
- RockPhos: Un ligando de fosfina basado en bifenilo, RockPhos, funciona con catalizadores Pd(0) para la formación de enlaces carbono-carbono y carbono-heteroátomo. Se ha utilizado en la 2-fluoroetoxilación de bromo-calconas y la conversión de cloruros de arilo a metoxidos de arilo .
Mecanismo De Acción
Target of Action
tBuBrettPhos is a dialkylbiaryl phosphine ligand . It is primarily targeted towards palladium , a transition metal, and is widely used in palladium-catalyzed cross-coupling reactions .
Mode of Action
tBuBrettPhos interacts with its target, palladium, to form a complex that acts as a precatalyst . This precatalyst promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems . The formation of the active catalytic species is efficient, and the ligand to palladium ratio can be accurately controlled .
Biochemical Pathways
The primary biochemical pathway influenced by tBuBrettPhos involves the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds . These bonds are crucial in the synthesis of various organic compounds. The compound’s action can affect multiple downstream effects, including the synthesis of complex organic molecules.
Pharmacokinetics
Its solubility in a wide range of common organic solvents suggests that it could have good distribution properties if used in a biological context.
Result of Action
The result of tBuBrettPhos’s action is the efficient promotion of cross-coupling reactions . This leads to the formation of various organic compounds, including those with C-C, C–N, C–O, C–F, C–CF3, and C–S bonds . It has been used as a precatalyst for the N-arylation of amino acid esters with aryl triflates under mild reaction conditions and minimal racemization of the amino acid ester .
Action Environment
tBuBrettPhos is air-, moisture-, and thermally-stable , suggesting that it can maintain its efficacy and stability under a variety of environmental conditions.
Actividad Biológica
tBuBrettPhos, a phosphine ligand, has garnered attention in the field of organometallic chemistry due to its significant role in catalysis, particularly in palladium-catalyzed reactions. This article explores the biological activity of tBuBrettPhos, focusing on its applications, mechanisms of action, and relevant research findings.
Chemical Structure and Properties
tBuBrettPhos is characterized by a bulky tert-butyl group that enhances its steric properties, making it a valuable ligand in various catalytic processes. Its structure allows for effective coordination with transition metals, facilitating reactions such as cross-coupling and C–S bond formation.
Biological Activity Overview
While tBuBrettPhos is primarily recognized for its catalytic applications, recent studies have begun to explore its biological implications. The biological activity can be categorized into several key areas:
- Catalytic Efficiency : tBuBrettPhos has shown high yields in palladium-catalyzed reactions, which are crucial in synthesizing biologically active compounds.
- Inhibition Studies : Research indicates potential inhibitory effects on certain biological pathways, although specific studies on direct biological targets remain limited.
1. Catalytic Applications
tBuBrettPhos has been extensively studied for its role in catalyzing C–S cross-coupling reactions. A study demonstrated that using tBuBrettPhos as a ligand resulted in yields exceeding 97% when applied to aryl thiol arylation reactions (Table 1) .
| Reaction Type | Yield (%) | Conditions |
|---|---|---|
| Aryl Thiol Arylation | 97% | Room temperature, 2 hours |
| C–N Cross-Coupling | 91% | Varying aryl halides |
2. Inhibition of CYP Enzymes
A study evaluated the inhibition potential of various phosphine ligands, including tBuBrettPhos, on cytochrome P450 enzymes (CYPs). While specific IC50 values for tBuBrettPhos were not reported, the study highlighted its role in modulating enzyme activity indirectly through catalytic pathways .
3. Mechanistic Insights
Research into the mechanistic aspects of tBuBrettPhos revealed that it enhances the stability of palladium catalysts under various reaction conditions. This stability is crucial for maintaining enzyme functionality during catalytic processes .
Discussion
The biological activity of tBuBrettPhos is primarily linked to its efficacy as a ligand in catalysis rather than direct biological interactions. Its ability to facilitate high-yield reactions makes it an essential compound in synthesizing pharmaceuticals and other biologically relevant molecules. However, more focused research is needed to elucidate any direct biological effects or interactions with specific biological targets.
Propiedades
IUPAC Name |
ditert-butyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C31H49O2P/c1-19(2)22-17-23(20(3)4)27(24(18-22)21(5)6)28-25(32-13)15-16-26(33-14)29(28)34(30(7,8)9)31(10,11)12/h15-21H,1-14H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
REWLCYPYZCHYSS-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C31H49O2P |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID70657989 |
Source
|
| Record name | Di-tert-butyl[3,6-dimethoxy-2',4',6'-tri(propan-2-yl)[1,1'-biphenyl]-2-yl]phosphane | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID70657989 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
484.7 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
1160861-53-9 |
Source
|
| Record name | Di-tert-butyl[3,6-dimethoxy-2',4',6'-tri(propan-2-yl)[1,1'-biphenyl]-2-yl]phosphane | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID70657989 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
Descargo de responsabilidad e información sobre productos de investigación in vitro
Tenga en cuenta que todos los artículos e información de productos presentados en BenchChem están destinados únicamente con fines informativos. Los productos disponibles para la compra en BenchChem están diseñados específicamente para estudios in vitro, que se realizan fuera de organismos vivos. Los estudios in vitro, derivados del término latino "in vidrio", involucran experimentos realizados en entornos de laboratorio controlados utilizando células o tejidos. Es importante tener en cuenta que estos productos no se clasifican como medicamentos y no han recibido la aprobación de la FDA para la prevención, tratamiento o cura de ninguna condición médica, dolencia o enfermedad. Debemos enfatizar que cualquier forma de introducción corporal de estos productos en humanos o animales está estrictamente prohibida por ley. Es esencial adherirse a estas pautas para garantizar el cumplimiento de los estándares legales y éticos en la investigación y experimentación.
