4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)benzoic acid

Base Information

• Chemical Name: 4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)benzoic acid
• CAS No.: 104561-41-3
• Molecular Formula: C₂₃H₂₄O₂
• Molecular Weight: 332.442
• UNII: VSDTYDJDJJ
• DSSTox Substance ID: DTXSID40438025
• Nikkaji Number: J390.100I
• Pharos Ligand ID: 8W7M81MJCU19
• ChEMBL ID: CHEMBL451835
• Mol file: 104561-41-3.mol

Synonyms:AGN 190205;AGN-190205

Chemical Property of 4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)benzoic acid

Chemical Property:

• Melting Point: 254-256 °C(Solv: acetonitrile (75-05-8))
• Boiling Point: 484.7±45.0 °C(Predicted)
• PKA: 4.10±0.10(Predicted)
• PSA: 37.30000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 5.13360
• Storage Temp.: Store at +4°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 332.177630004
• Heavy Atom Count: 25
• Complexity: 565

Purity/Quality:

99%+, ^*data from raw suppliers

EC23 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(C2=C1C=CC(=C2)C#CC3=CC=C(C=C3)C(=O)O)(C)C)C
• Uses: EC 23 is an ATRA analog with similar activity. EC 23 potently induces neural differentiation in human pluripotent embryonic stem cells.

Technology Process of 4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)benzoic acid

There total 4 articles about 4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl)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: 72.0%

4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid methyl ester (1010385-77-9) → 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl]benzoic acid (104561-41-3)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 70 ℃; for 20h;

DOI:10.1039/b808574a

Reference yield: 28.0%

4-iodobenzoic acid (619-58-9) → 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl]benzoic acid (104561-41-3)

Guidance literature:

With CuI; triethylamine; Pd(PPh₃)2Cl₂;

Reference yield: 20.0%

4-iodobenzoic acid (619-58-9) + 6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (119362-54-8) → 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl]benzoic acid (104561-41-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 7h;

DOI:10.1016/j.bmcl.2008.11.040

upstream raw materials:

4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid methyl ester

4-iodobenzoic acid

6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Refernces

• 1、 Charton, Julie,Deprez-Poulain, Rebecca,Hennuyer, Nathalie,Tailleux, Anne,Staels, Bart,Deprez, Benoit. "Novel non-carboxylic acid retinoids: 1,2,4-Oxadiazol-5-one derivatives". supporting information; experimental part. p. 489 - 492. Retrieved 2011/02/28.
• 2、 -. "Diarylacetylenes, their preparation and their use". . . Retrieved 2008/06/13.