(Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one

Base Information

• Chemical Name: (Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one
• CAS No.: 218768-11-7
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.274
• European Community (EC) Number: 700-075-6,815-956-1
• DSSTox Substance ID: DTXSID101197661
• Wikidata: Q76511760
• Mol file: 218768-11-7.mol

Synonyms:218768-11-7;73356-31-7;(Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one;4-Hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one;(3Z)-4-Hydroxy-4-(6-methoxy-2-naphthalenyl)-3-buten-2-one;4-(6'-methoxy-2-naphthyl)-4-hydroxy-but-3-en-2-one;3-Buten-2-one, 4-hydroxy-4-(6-methoxy-2-naphthalenyl)-, (3Z)-;4-(6-Methoxy-2-naphthyl)-4-hydroxy-3-buten-2-one;SCHEMBL7742061;(3Z)-4-HYDROXY-4-(6-METHOXYNAPHTHALEN-2-YL)BUT-3-EN-2-ONE;DTXSID101197661;NS00006880;EC 700-075-6;3-Buten-2-one,4-hydroxy-4-(6-methoxy-2-naphthalenyl)-,(3Z)-

Chemical Property of (Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one

Chemical Property:

• Vapor Pressure: 5.37E-09mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 453°Cat760mmHg
• Flash Point: 173.4°C
• PSA: 46.53000
• Density: 1.193g/cm³
• LogP: 3.33630
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 335

Purity/Quality:

99.9% ^*data from raw suppliers

(3Z)-4-Hydroxy-4-(6-methoxy-2-naphthalenyl)-3-buten-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C=C(C1=CC2=C(C=C1)C=C(C=C2)OC)O
• Isomeric SMILES: CC(=O)/C=C(/C1=CC2=C(C=C1)C=C(C=C2)OC)\O
• Uses: (3Z)-4-Hydroxy-4-(6-methoxy-2-naphthalenyl)-3-buten-2-one is derived from 6-Methoxy-2-naphthalenecarboxaldehyde (M264760), which is used as a diagnostic reagent in tumor studies involving aldehyde dehydrogenase enzymes. In addition it is used in organic synthesis reactions forming fluorescent substrates for inhibition studies relating to hypertension and vascular inflammation.This compound is suitable for aldehyde dehydrogenase (ALDH) related research.

Technology Process of (Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one

There total 2 articles about (Z)-4-hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one 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%

6-methoxy-2-acetylnaphthalene (3900-45-6) + ethyl acetate (141-78-6) → 4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one (73356-31-7,218768-11-7)

Guidance literature:

6-methoxy-2-acetylnaphthalene; ethyl acetate; With potassium sec-butoxide; In dimethyl sulfoxide; at 50 - 60 ℃; for 1h;

With hydrogenchloride; In water; dimethyl sulfoxide; pH=2; Reagent/catalyst;

DOI:10.1021/op980060d

Reference yield: 84.0%

6-methoxy-2-acetylnaphthalene (3900-45-6) → 4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one (73356-31-7,218768-11-7)

Guidance literature:

With hydrogenchloride; In dimethyl sulfoxide; ethyl acetate;

Reference yield: 65.0%

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one (73356-31-7,218768-11-7) → 4-(6-methoxynaphthalen-2-yl)butan-2-ol (65726-24-1) + nabumetone (42924-53-8) + (±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone (220786-56-1,98386-83-5)

Guidance literature:

With sulfuric acid; palladium 10% on activated carbon; hydrogen; In ethyl acetate;

DOI:10.1021/op980060d

upstream raw materials:

6-methoxy-2-acetylnaphthalene

ethyl acetate

Downstream raw materials:

(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone

4-(6-methoxynaphthalen-2-yl)butan-2-ol

nabumetone

4-(2-methoxynaphthalene-6-yl)but-3-en-2-one