Benzenepropanoic acid, b-2-propynyl-

Base Information

• Chemical Name: Benzenepropanoic acid, b-2-propynyl-
• CAS No.: 92898-16-3
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• Mol file: 92898-16-3.mol

Synonyms:3-Phenyl-hex-5-ynoic acid;

Chemical Property of Benzenepropanoic acid, b-2-propynyl-

Chemical Property:

• PSA: 37.30000
• LogP: 2.26820

Purity/Quality:

3-Phenylhex-5-ynoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanoic acid, b-2-propynyl-

There total 8 articles about Benzenepropanoic acid, b-2-propynyl- 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: 88.0%

2-(1-Phenyl-but-3-ynyl)-malonic acid (99512-37-5) → 3-phenyl-5-hexynoic acid (92898-16-3)

Guidance literature:

In m-xylene; at 135 ℃; for 2.75h;

DOI:10.1021/jm00152a011

Reference yield: 80.0%

5,6-Dibromo-3-phenyl-hexanoic acid ethyl ester (122019-83-4) → 3-phenyl-5-hexynoic acid (92898-16-3)

Guidance literature:

With potassium hydroxide; In methanol; water; for 60h; Heating;

DOI:10.1021/jo00277a040

Reference yield:

1-phenylbut-3-yn-1-ol (1743-36-8) → 3-phenyl-5-hexynoic acid (92898-16-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / 0.17 h

2: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, a) reflux, 6.5 h, b) 25 deg C, 18 h

3: 96 percent / 10percent aq. KOH / methanol / 16 h / 25 °C

4: 88 percent / m-xylene / 2.75 h / 135 °C

With potassium hydroxide; sodium hydride; triethylamine; In methanol; m-xylene;

DOI:10.1021/jm00152a011

upstream raw materials:

5,6-Dibromo-3-phenyl-hexanoic acid ethyl ester

2-(1-Phenyl-but-3-ynyl)-malonic acid

1-phenylbut-3-yn-1-ol

rac-diethyl 2-(1-phenyl-3-butynyl)-malonate

Downstream raw materials:

4-phenyl-6-methyl-3,4-dihydro-2-pyranone

N-((1R)-1-phenyl-2-hydroxyethyl)-5-oxo-3-phenylhexanamide

(3S)-3-phenyl-5-hexynoic acid

(4S)-4-phenyl-6-methylidenetetrahydro-2-pyranone

Refernces

• 1、 Sofia, Michael J.,Katzenellenbogen, John A.. "Enol Lactone Inhibitors of Serine Proteases. The Effect of Regiochemistry on the Inactivation Behavior of Phenyl-Substituted (Halomethylene)tetra- and -dihydrofuranones and (Halomethylene)tetrahydropyranones toward α-Chymotrypsin: Stable Acyl Enzyme Inter". . p. 230 - 238. Retrieved 2007/10/02.