(2e,4e,6z)-3-Methyl-7-(5,5,8,8-Tetramethyl-3-Propoxy-5,6,7,8-Tetrahydronaphthalen-2-Yl)octa-2,4,6-Trienoic Acid

Base Information

• Chemical Name: (2e,4e,6z)-3-Methyl-7-(5,5,8,8-Tetramethyl-3-Propoxy-5,6,7,8-Tetrahydronaphthalen-2-Yl)octa-2,4,6-Trienoic Acid
• CAS No.: 180713-37-5
• Molecular Formula: C₂₆H₃₆O₃
• Molecular Weight: 396.57
• Nikkaji Number: J763.589C
• Wikidata: Q27080268
• Pharos Ligand ID: ZTH9MPJPQ1FS
• ChEMBL ID: CHEMBL109581
• Mol file: 180713-37-5.mol

Synonyms:7-(3-n-propoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-3-methylocta-2,4,6-trienoic acid;7-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy)naphthalen-3-yl)-3-methylocta-2,4,6-trienoic acid;LG 100754;LG100754;LG754

Chemical Property of (2e,4e,6z)-3-Methyl-7-(5,5,8,8-Tetramethyl-3-Propoxy-5,6,7,8-Tetrahydronaphthalen-2-Yl)octa-2,4,6-Trienoic Acid

Chemical Property:

• Vapor Pressure: 6.63E-13mmHg at 25°C
• Boiling Point: 549.4°C at 760 mmHg
• PKA: 4.74±0.33(Predicted)
• Flash Point: 178.5°C
• PSA: 46.53000
• Density: 1.003g/cm³
• LogP: 6.81480
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 396.26644501
• Heavy Atom Count: 29
• Complexity: 665

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

LG 100754 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCOC1=CC2=C(C=C1C(=CC=CC(=CC(=O)O)C)C)C(CCC2(C)C)(C)C
• Isomeric SMILES: CCCOC1=CC2=C(C=C1/C(=C\C=C\C(=C\C(=O)O)\C)/C)C(CCC2(C)C)(C)C
• Description: LG 100754 is a ligand of retinoid X receptor (RXR) that modulates the activity of RXR dimers. It acts as an antagonist towards RXR homodimers but as an agonist of heterodimers consisting of RXR and retinoic acid receptor (RAR) or PPARs. LG 100754, at 1 μM, is a weak agonist of RXR-PPARγ but strongly enhances signaling through the heterodimer in response to PPARγ ligands, including rosiglitazone and 15-deoxy-Δ12,14-prostaglandin J2 . Through this action, LG 100754 decreases glucose levels and relieves insulin resistance in mice.
• Uses: LG 100754 is a novel RXR:PPARγ agonist and decreases glucose levels in vivo. It can also be used in compositions comprising anti-androgen and anti-thyroid agents and kits for diagnosis and treatment of viral respiratory infection.

Technology Process of (2e,4e,6z)-3-Methyl-7-(5,5,8,8-Tetramethyl-3-Propoxy-5,6,7,8-Tetrahydronaphthalen-2-Yl)octa-2,4,6-Trienoic Acid

There total 17 articles about (2e,4e,6z)-3-Methyl-7-(5,5,8,8-Tetramethyl-3-Propoxy-5,6,7,8-Tetrahydronaphthalen-2-Yl)octa-2,4,6-Trienoic 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: 88.0%

triethyl 3-methyl-4-phosphonocrotonate (39760-56-0,3917-43-9,41891-54-7) + (2Z)-3-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy)naphthalen-3-yl]but-2-en-1-al (180861-54-5) → LG100754 (180713-37-5)

Guidance literature:

triethyl 3-methyl-4-phosphonocrotonate; (2Z)-3-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy)naphthalen-3-yl]but-2-en-1-al; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; at -78 ℃;

With potassium hydroxide; In methanol; Further stages.; Heating;

DOI:10.1021/jo991936x

Reference yield:

(2E,4E,6Z)-7-3[-propoxy-5,6,7,8-tetrahydro 5,5,8,8-tetramethyl-2-naphthalene-2-yl]-3-methyl-octa-2,4,6-trienoic acid ethyl ester → LG100754 (180713-37-5)

Guidance literature:

With methanol; potassium hydroxide; at -78 - 0 ℃; for 0.25h; Reflux;

Reference yield:

5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol (22824-31-3) → LG100754 (180713-37-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / 75percent H₂SO₄ / 3 h / 100 °C

2.1: 99 percent / LiAlH₄ / diethyl ether / 3 h / 0 - 20 °C

3.1: 98 percent / CsF / dimethylformamide / 15 h / 20 °C

4.1: 90 percent / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

5.1: n-BuLi; DMPU / tetrahydrofuran / -78 °C

5.2: 88 percent / KOH / methanol / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; cesium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: Ring cleavage / 3.1: Alkylation / 4.1: Oxidation / 5.1: Condensation / 5.2: Hydrolysis;

DOI:10.1021/jo991936x

upstream raw materials:

(2E,4E,6Z)-3-Methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester

triethyl 3-methyl-4-phosphonocrotonate

(2Z)-3-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-(n-propyloxy)naphthalen-3-yl]but-2-en-1-al

1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylbenzo[5,6-g]coumarin

Refernces

• 1、 -. "EXPANSION OF RENEWABLE STEM CELL POPULATIONS". . . Retrieved 2016/05/02.