(5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione

Base Information

• Chemical Name: (5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione
• CAS No.: 5989-48-0
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.306
• DSSTox Substance ID: DTXSID90417300
• Wikidata: Q82227114
• Mol file: 5989-48-0.mol

Synonyms:5989-48-0;(5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione;AC1NT64N;DTXSID90417300;CCG-13512;AKOS000409776;BIM-0017694.P001;SR-01000224944;SR-01000224944-1

Chemical Property of (5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.633g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 368.00078
• Heavy Atom Count: 22
• Complexity: 521

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C(=CC(=C1)C=C2C(=O)NC(=O)N(C2=O)C)Br)O
• Isomeric SMILES: CCOC1=C(C(=CC(=C1)/C=C\2/C(=O)NC(=O)N(C2=O)C)Br)O

Technology Process of (5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione

There total 12 articles about (5Z)-5-[(3-bromo-5-ethoxy-4-hydroxyphenyl)methylidene]-1-methyl-1,3-diazinane-2,4,6-trione 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%

rac-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl vinyl ether → menthol (89-78-1) + (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8) + (1R,2S,4S)-1-isopropyl-4-methyl-2-(vinyloxy)cyclohexane (7637-11-8)

Guidance literature:

With water; C₂H₃O₂^(1-)*C₃₆H₅₃CoN₂O₂⁽¹⁺⁾; In methanol; at -10 ℃; for 2h; Product distribution / selectivity;

Reference yield: 81.0%

vinyl acetate (108-05-4,9003-20-7) + (-)-menthol (2216-51-5) → (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; In toluene; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2012.02.025

Reference yield: 75.0%

acetaldehyde ethyl menthyl acetal (363603-37-6) → (1S,2R,4R)-1-isopropyl-4-methyl-(2-vinyloxy)cyclohexane (5989-48-0,7637-09-4,7637-10-7,7637-11-8,23960-73-8,46173-76-6,127642-93-7,3885-03-8) + (-)-menthol trimethylsilyl ether (18419-38-0,62338-23-2,88390-70-9,122999-13-7,66808-39-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 20 ℃; for 15h; Yields of byproduct given;

DOI:10.1016/0040-4039(95)00087-S

upstream raw materials:

(-)-menthol

acetylene

butan-1-ol

ethyl vinyl ether

Downstream raw materials:

[(1S,3S,4S)-4-Dimethoxymethyl-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-(2,4-dinitro-phenyl)-amine

[(1R,3R,4R)-4-Dimethoxymethyl-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-(2,4-dinitro-phenyl)-amine

acetaldehyde

2-menthoxyethylamine