Ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate

Base Information

• Chemical Name: Ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate
• CAS No.: 82258-36-4
• Molecular Formula: C17H23ClO4
• Molecular Weight: 326.82
• DSSTox Substance ID: DTXSID60869695
• Nikkaji Number: J25.813J
• Wikipedia: Etomoxir
• Wikidata: Q19904108
• NCI Thesaurus Code: C81111
• ChEMBL ID: CHEMBL1531556
• Mol file: 82258-36-4.mol

Synonyms:ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate;etomoxir

Chemical Property of Ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate

Chemical Property:

• Vapor Pressure: 9.04E-07mmHg at 25°C
• Boiling Point: 405°Cat760mmHg
• Flash Point: 142.6°C
• PSA: 48.06000
• Density: 1.163g/cm³
• LogP: 4.00140
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 326.1284869
• Heavy Atom Count: 22
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

rac-Etomoxir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CO1)CCCCCCOC2=CC=C(C=C2)Cl
• Uses: An inhibitor of carnitine palmitoyltransferase A (CPT1), which is required for the oexidation of long-chain acyl CoA esters. A strong inhibitor of mitochondrial CPT1 and is a candidate as an anti-diabetic drug.

Technology Process of Ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate

There total 8 articles about Ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate 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: 50.0%

ethyl 2-[6-(p-chlorophenoxy)hexyl]acrylate (82258-37-5) → 2-(6-(4-chlorophenoxy)-hexyl)-oxirane-2-carboxylic acid ethyl ester (82258-36-4,828934-40-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; for 48h; Heating;

DOI:10.1016/S0040-4039(00)01967-5

Reference yield:

(Z)-2-Bromomethyl-8-(4-chloro-phenoxy)-oct-2-enoic acid ethyl ester → 2-(6-(4-chlorophenoxy)-hexyl)-oxirane-2-carboxylic acid ethyl ester (82258-36-4,828934-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DABCO / H₂O; tetrahydrofuran / 0.25 h / 20 °C

1.2: 73 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 20 °C

2.1: 50 percent / m-CPBA / 1,2-dichloro-ethane / 48 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)01967-5

Reference yield:

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → 2-(6-(4-chlorophenoxy)-hexyl)-oxirane-2-carboxylic acid ethyl ester (82258-36-4,828934-40-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) NaH / 1) THF, RT, 10 min, 2) THF, 70 deg C, 10 h

2: 99.4 percent / KOH / ethanol / 30 h / Ambient temperature

3: 1) NaH / 1) THF, Rt, 30 min, 2) THF, 24 h, 70 deg C

4: 72.3 percent / Na₂EDTA, NaHCO₃, Oxone, MeCOCF₃ / acetonitrile / 0.5 h / 0 °C

5: 76.6 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 55 °C

6: 80.4 percent / PPh₃, DEAD / tetrahydrofuran / 2 h / Ambient temperature

With Oxone; potassium hydroxide; 1,1,1-trifluoro-2-propanone; pyridinium p-toluenesulfonate; edetate disodium; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.3987/COM-98-8150

upstream raw materials:

ethyl 2-[6-(p-chlorophenoxy)hexyl]acrylate

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

diethyl 2-<6-(tetrahydro-2H-pyranyloxy)hexyl>malonate

ethyl 2-<6-(tetrahydro-2H-pyranyloxy)hexyl>acrylate

Refernces

• 1、 Suh, Young-Ger,Min, Kyung-Hoon,Back, So-Young,Chai, Jung-Hyeon. "Versatile synthesis of 2-aryloxyalkyl-oxirane-2-carboxylate: Syntheses of ethyl 2-[6-(3-alkoxyphenoxy)-hexyl]oxirane-2-carboxylates". . p. 1527 - 1535. Retrieved 2007/10/03.
• 2、 -. "Phospholipase A2 inhibitors". . . Retrieved 2008/06/13.