(4S)-4-tert-butyl-2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazole

Base Information

• Chemical Name: (4S)-4-tert-butyl-2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazole
• CAS No.: 137542-80-4
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• DSSTox Substance ID: DTXSID901128442
• Nikkaji Number: J432.666K
• Mol file: 137542-80-4.mol

Synonyms:DTXSID901128442;137542-80-4;Oxazole, 4-(1,1-dimethylethyl)-4,5-dihydro-2-[2-(2-methoxyphenyl)ethenyl]-, [S-(E)]-

Chemical Property of (4S)-4-tert-butyl-2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazole

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 354

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1COC(=N1)C=CC2=CC=CC=C2OC
• Isomeric SMILES: CC(C)(C)[C@H]1COC(=N1)/C=C/C2=CC=CC=C2OC

Technology Process of (4S)-4-tert-butyl-2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazole

There total 3 articles about (4S)-4-tert-butyl-2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,5-dihydro-1,3-oxazole 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: 70.0%

((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-ylmethyl)-phosphonic acid diethyl ester (137542-75-7) + ortho-anisaldehyde (135-02-4) → (4S)-4-tert-butyl-2-<(E)-2-(2-methoxyphenyl)ethenyl>-2-oxazoline (137542-80-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; for 42h;

DOI:10.1021/jo00025a027

Reference yield:

(S)-4-tert-butyl-2-methyl-Δ2-oxazoline (137542-74-6) → (4S)-4-tert-butyl-2-<(E)-2-(2-methoxyphenyl)ethenyl>-2-oxazoline (137542-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA / 1) THF, hexane, -78 deg C, 1h, 2a) -78 deg C, 1h, 2b) to 0 deg C

2: 70 percent / LiCl, DBU / acetonitrile / 42 h

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium diisopropyl amide; In acetonitrile;

DOI:10.1021/jo00025a027

Reference yield:

(S)-tert-leucinol (112245-13-3) → (4S)-4-tert-butyl-2-<(E)-2-(2-methoxyphenyl)ethenyl>-2-oxazoline (137542-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / CH₂Cl₂ / Ambient temperature

2: 1) LDA / 1) THF, hexane, -78 deg C, 1h, 2a) -78 deg C, 1h, 2b) to 0 deg C

3: 70 percent / LiCl, DBU / acetonitrile / 42 h

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium diisopropyl amide; In dichloromethane; acetonitrile;

DOI:10.1021/jo00025a027

upstream raw materials:

((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-ylmethyl)-phosphonic acid diethyl ester

ortho-anisaldehyde

(S)-tert-leucinol

(S)-4-tert-butyl-2-methyl-Δ²-oxazoline

Downstream raw materials:

(S)-4-tert-Butyl-2-[(R)-2-(2-methoxy-phenyl)-hexyl]-4,5-dihydro-oxazole

(R)-3-(2-Methoxy-phenyl)-heptan-1-ol

(3R)-3-(2-methoxyphenyl)heptanal

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-3-(2-methoxy-phenyl)-heptyl ester