(S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole

Base Information

• Chemical Name: (S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole
• CAS No.: 148461-16-9
• Molecular Formula: C25H26 N O P
• Molecular Weight: 387.461
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70433043
• Nikkaji Number: J601.288D
• Wikidata: Q72470363
• Mol file: 148461-16-9.mol

Synonyms:148461-16-9;(S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole;(S)-4-TERT-BUTYL-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-2-OXAZOLINE;(S)-4-tert-Butyl-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole;[2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]-diphenylphosphane;(4S)-4-tert-Butyl-2-[2-(diphenylphosphanyl)phenyl]-4,5-dihydro-1,3-oxazole;(S)-t-BuPHOX;(S)-tBu-Phox;C25H26NOP;SCHEMBL1111225;DTXSID70433043;DMOLTNKQLUAXPI-HSZRJFAPSA-N;YFA46116;MFCD09998277;AKOS016845941;AS-72502;CS-0029503;A911337;J-008473;2-[2-(Diphenylphosphino)phenyl]-4beta-tert-butyl-2-oxazoline;(S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline, 97%

Chemical Property of (S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole

Chemical Property:

• Melting Point: 111-116 °C
• Boiling Point: 498.9±28.0 °C(Predicted)
• PKA: 4.44±0.70(Predicted)
• PSA: 35.18000
• LogP: 4.07190
• Storage Temp.: ?20°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 387.175201451
• Heavy Atom Count: 28
• Complexity: 509

Purity/Quality:

97% ^*data from raw suppliers

(S)-t-BuPHOX ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1COC(=N1)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: CC(C)(C)[C@H]1COC(=N1)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: (S)-4-Tert-Butyl-2-(2-(Diphenylphosphino)Phenyl)-4,5-Dihydrooxazole (cas# 148461-16-9) is a useful research chemical. (S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline can be used as a ligand for enantioselective Heck reaction without any C=C double bond migration byproduct. It can also be used in a rhodium(I)-catalyzed enantioselective desymmetrization reaction of meso-3,5-dimethyl glutaric anhydride, to form substituted syn-deoxypolypropionate fragments in a single transformation.

Technology Process of (S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole

There total 24 articles about (S)-4-(tert-Butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-tert-butyl-2-(2-fluorophenyl)-4,5-dihydro-oxazole (150255-49-5) + potassium diphenylphosphine (15475-27-1,4346-39-8) → (S)-4-(tert-butyl)-2-(2-(diphenylphosphaneyl)phenyl)-4,5-dihydrooxazole (148461-16-9)

Guidance literature:

In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)93403-8

Reference yield: 88.0%

2-(2-bromophenyl)-4-(1,1-dimethylethyl)-4,5-dihydro-(4S)-oxazole (154701-60-7) + diphenylphosphane (829-85-6) → (S)-4-(tert-butyl)-2-(2-(diphenylphosphaneyl)phenyl)-4,5-dihydrooxazole (148461-16-9)

Guidance literature:

diphenylphosphane; With copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 20 ℃; for 0.333333h; Inert atmosphere;

2-(2-bromophenyl)-4-(1,1-dimethylethyl)-4,5-dihydro-(4S)-oxazole; With caesium carbonate; In toluene; at 110 ℃; for 21h; Inert atmosphere; Sealed vessel;

Reference yield: 73.0%

2-(diphenylphosphanyl)benzonitrile (34825-99-5) + (S)-tert-leucinol (112245-13-3) → (S)-4-(tert-butyl)-2-(2-(diphenylphosphaneyl)phenyl)-4,5-dihydrooxazole (148461-16-9)

Guidance literature:

With zinc(II) chloride; In chlorobenzene; for 144h; Reflux;

DOI:10.1021/acs.orglett.1c03227

upstream raw materials:

4-tert-butyl-2-(2-fluorophenyl)-4,5-dihydro-oxazole

potassium diphenylphosphine

2-(diphenylphosphanyl)benzonitrile

(S)-tert-leucinol

Refernces

Unusual allylpalladium carboxylate complexes: Identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones

10.1002/anie.200902575

The research investigates the catalytic enantioselective allylic alkylation reactions of cyclic ketone enolates. The study focuses on the decarboxylation of allyl carbonates and β-ketoesters, aiming to identify the resting state of the catalytic cycle. Key chemicals involved in the research include (S)-tBu-phox (3), [Pd2(dba)3], β-ketoester (±)-2, and dba. Through 31P NMR spectroscopy, the researchers observed the formation of a long-lived intermediate complex 1, which was isolated and characterized as a square-planar 16-electron species with a σ-bound, η1-allyl ligand and a β-ketocarboxylate ligand. This complex was identified as the resting state of the reaction. The study also involved the synthesis and characterization of related complexes, such as neutral [(tBu-phox)Pd(η1-allyl)(OAc)] (7) and [Pd(tBu-phox)(dba)] (5), to elucidate the mechanistic pathway of the allylic alkylation reaction. The findings provide insights into the decarboxylation step as the rate-determining step and offer a detailed understanding of the catalytic cycle, with potential implications for other palladium-catalyzed transformations.