![molecular formula C31H49O2P B580627 Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphin CAS No. 1160861-53-9](/img/structure/B580627.png)
Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphin
Übersicht
Beschreibung
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%.
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Wissenschaftliche Forschungsanwendungen
N-Arylierung von Aminosäureestern
tBuBrettPhos wurde als Präkatalysator für die N-Arylierung von Aminosäureestern unter Verwendung von Aryltriflaten eingesetzt. Bemerkenswert ist, dass diese Reaktion unter milden Bedingungen abläuft und die Racemisierung des Aminosäureesters minimiert. Die Fähigkeit, Arylreste selektiv in Aminosäurederivate einzuführen, ist in der pharmazeutischen Chemie und Peptidsynthese wertvoll .
Umwandlung von Arylhalogeniden zu Phenolen
In Gegenwart von Benzaldoxim als Hydroxid-Surrogat katalysiert tBuBrettPhos die Umwandlung von Arylhalogeniden (wie Arylchloriden und -bromiden) zu Phenolen. Diese Transformation bietet einen direkten Weg zu Phenolverbindungen, die Anwendungen in der Pharmazeutik, Agrochemie und Materialwissenschaft finden .
C-C, C-N und C-O-Bindungsbildung
tBuBrettPhos ist sehr vielseitig in der Bildung verschiedener Bindungen über palladiumkatalysierte Kreuzkupplungsreaktionen:
- C-O-Bindungsbildung: Es fördert die Arylierung von Alkoholen, Phenolen und anderen sauerstoffhaltigen Substraten, wodurch wertvolle Produkte entstehen .
Stabilität und Löslichkeit
- Löslichkeit: Es löst sich gut in einer Vielzahl organischer Lösungsmittel, was seine Anwendbarkeit unter verschiedenen Reaktionsbedingungen erhöht .
Weitere Buchwald-Präkatalysatoren
Während tBuBrettPhos ein Starspieler ist, wollen wir kurz ein paar verwandte Präkatalysatoren erwähnen:
- tBuXPhos: Ein weiterer Buchwald-Ligand, tBuXPhos, verstärkt die Pd-katalysierte C-O- und C-N-Bindungsbildung. Es findet Anwendungen bei Tsuji-Trost-Substitutionen, Kreuzkupplungen von benzylischen Fluoriden und C-N-Kupplungsreaktionen mit Sulfinamiden und Arylhalogeniden .
- RockPhos: Ein biphenylbasierter Phosphinligand, RockPhos, arbeitet mit Pd(0)-Katalysatoren zur Bildung von Kohlenstoff-Kohlenstoff- und Kohlenstoff-Heteroatom-Bindungen. Es wurde bei der 2-Fluorethoxylierung von Brom-Chalkonen und der Umwandlung von Arylchloriden zu Arylmethoxiden eingesetzt .
Wirkmechanismus
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.
Biologische Aktivität
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.
Eigenschaften
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. | |
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