(4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE

Base Information

• Chemical Name: (4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE
• CAS No.: 148461-12-5
• Molecular Formula: C₂₂H₂₀NOP
• Molecular Weight: 345.381
• Mol file: 148461-12-5.mol

Synonyms:Oxazole,2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-methyl-, (S)-

Chemical Property of (4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE

Chemical Property:

• Melting Point: 85-90 °C
• Boiling Point: 474.2±28.0 °C(Predicted)
• PKA: 4.44±0.70(Predicted)
• PSA: 35.18000
• LogP: 3.68180

Purity/Quality:

98%Min ^*data from raw suppliers

(4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE

There total 6 articles about (4S)-(-)-4,5-DIHYDRO-2-[2'-(DIPHENYLPHOSPHINO)PHENYL]-4-ISOPROPYLOXAZOLE 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: 80.0%

(-)-(S)-2-(2-fluoro-phenyl)-4-methyl-4,5-dihydro-oxazole (150255-45-1) + potassium diphenylphosphine (15475-27-1,4346-39-8) → (-)-(S)-2-(2-diphenylphosphino-phenyl)-4-methyl-4,5-dihydro-oxazole (148461-12-5)

Guidance literature:

In tetrahydrofuran; Heating;

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

Reference yield:

2-fluorobenzonitrile (394-47-8) → (-)-(S)-2-(2-diphenylphosphino-phenyl)-4-methyl-4,5-dihydro-oxazole (148461-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / ZnCl₂ / chlorobenzene / 48 h / Heating

2: 80 percent / tetrahydrofuran / 2 h / Heating

zinc(II) chloride; In tetrahydrofuran; chlorobenzene;

DOI:10.1016/S0040-4020(01)80795-X

Reference yield:

(1'S)-2-fluoro-N-<1-(hydroxymethyl)ethyl>benzamide (111904-32-6) → (-)-(S)-2-(2-diphenylphosphino-phenyl)-4-methyl-4,5-dihydro-oxazole (148461-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / SOCl₂ / toluene / 1 h / Heating

2: 96 percent / NaOH / methanol / 3 h / Heating

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane a) -20 deg C, 2 h, b) RT, overnight

With sodium hydroxide; n-butyllithium; thionyl chloride; In methanol; toluene;

DOI:10.1016/0040-4020(96)00267-0

upstream raw materials:

(-)-(S)-2-(2-fluoro-phenyl)-4-methyl-4,5-dihydro-oxazole

potassium diphenylphosphine

diphenylphosphane

(1'S)-2-fluoro-N-<1-(hydroxymethyl)ethyl>benzamide

Refernces

• 1、 Allen, Joanne V.,Coote, Steven J.,Dawson, Graham J.,Frost, Christopher G.,Martin, Christopher J.,Williams, Jonathon, M.. "Palladium-catalysed Asymmetric Allylic Substitution: a Ligand Design Incorporating Steric and Electronic Effects". . p. 2065 - 2072. Retrieved 2007/10/02.
• 2、 Dawson, Graham J.,Frost, Christopher G.,Williams, Jonathan M. J.,Coote, Steven J.. "Asymmetric Palladium Catalysed Allylic Substitution Using Phosphorus Containing Oxazoline Ligands". . p. 3149 - 3150. Retrieved 2007/10/02.