4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid

Base Information

• Chemical Name: 4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid
• CAS No.: 123065-77-0
• Molecular Formula: C₂₀H₂₀O₂S
• Molecular Weight: 324.444
• ChEMBL ID: CHEMBL118754
• DSSTox Substance ID: DTXSID101133237
• Nikkaji Number: J338.992H
• Pharos Ligand ID: 781GL25W264Z
• Mol file: 123065-77-0.mol

Synonyms:CHEMBL118754;SCHEMBL7825869;DTXSID101133237;BDBM50066907;4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid;123065-77-0;4-[(1E)-2-(2,3-Dihydro-3,3-dimethylbenzo[b]thien-5-yl)-1-propen-1-yl]benzoic acid

Chemical Property of 4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid

Chemical Property:

• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 324.11840105
• Heavy Atom Count: 23
• Complexity: 474

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CC1=CC=C(C=C1)C(=O)O)C2=CC3=C(C=C2)SCC3(C)C
• Isomeric SMILES: C/C(=C\C1=CC=C(C=C1)C(=O)O)/C2=CC3=C(C=C2)SCC3(C)C

Technology Process of 4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid

There total 6 articles about 4-[(E)-2-(3,3-Dimethyl-2,3-dihydro-benzo[b]thiophen-5-yl)-propenyl]-benzoic acid 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: 61.7%

methyl (E)-4-<2-(2,3-dihydro-3,3-dimethylbenzothien-5-yl)-1-propenyl>benzoate (123065-78-1) → (E)-4-[2-(2,3-dihydro-3,3-dimethylbenzo[b]thien-5-yl)-1-propenyl]benzoic acid (123065-77-0)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 0.916667h; Heating;

DOI:10.1021/jm00105a065

Reference yield:

2-methyl-1-(phenylthio)propan-2-ol (13307-60-3) → (E)-4-[2-(2,3-dihydro-3,3-dimethylbenzo[b]thien-5-yl)-1-propenyl]benzoic acid (123065-77-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 72.8 percent / AlCl₃ / CS₂ / 3 h / Heating

2: 88.9 percent / AlCl₃ / CS₂ / 2 h / Ambient temperature

3: LiAlH₄ / diethyl ether / 24 h / Heating

4: 70.3 percent / methanol / 36 h / Ambient temperature

5: 1.) n-BuLi / 1.) THF, hexane, RT, 1.5 h, 2.) 25 h

6: 61.7 percent / KOH / ethanol; H₂O / 0.92 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; In methanol; carbon disulfide; diethyl ether; ethanol; water;

DOI:10.1021/jm00105a065

Reference yield:

<1-(2,3-dihydro-3,3-dimethylbenzothien-5-yl)ethyl>triphenylphosphonium bromide (132102-36-4) → (E)-4-[2-(2,3-dihydro-3,3-dimethylbenzo[b]thien-5-yl)-1-propenyl]benzoic acid (123065-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / H₂, acetic acid / 10percent Pd/C / ethyl acetate

2: 1.) isobutyl chloroformate, N-methylmorpholine, 2.) N-methylmorpholine / 1.) THF, -20 deg C, 3 min, 2.) -20 deg C, 2 h

With 4-methyl-morpholine; hydrogen; acetic acid; isobutyl chloroformate; palladium on activated charcoal; In ethyl acetate;

upstream raw materials:

methyl (E)-4-<2-(2,3-dihydro-3,3-dimethylbenzothien-5-yl)-1-propenyl>benzoate

2-methyl-1-(phenylthio)propan-2-ol

<1-(2,3-dihydro-3,3-dimethylbenzothien-5-yl)ethyl>triphenylphosphonium bromide

2,3-dihydro-3,3-dimethylbenzo[b]thiophene