(2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic acid

Base Information

• Chemical Name: (2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic acid
• CAS No.: 80514-96-1
• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.266
• Mol file: 80514-96-1.mol

Synonyms:(2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic acid;2,4-Hexadienedioic acid, mono(5-methoxy-3-methyl-5-oxo-3-pentenyl) ester, (E,E,Z)-;80514-96-1

Chemical Property of (2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic acid

Chemical Property:

• Vapor Pressure: 3.81E-09mmHg at 25°C
• Boiling Point: 444.6°C at 760 mmHg
• Flash Point: 165.7°C
• Density: 1.19g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 268.09468823
• Heavy Atom Count: 19
• Complexity: 417

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC)CCOC(=O)C=CC=CC(=O)O
• Isomeric SMILES: C/C(=C/C(=O)OC)/CCOC(=O)/C=C/C=C/C(=O)O

Technology Process of (2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic acid

There total 4 articles about (2E,4E)-6-((Z)-5-Methoxy-3-methyl-5-oxopent-3-enoxy)-6-oxohexa-2,4-dienoic 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: 83.0%

5-hydroxy-2-(5H)-furanone (14032-66-7) + methyl (E)-3-methyl-5-<(di-O-methylphosphono)acetoxy>pent-2-enoate (80515-01-1) → (2E,4Z)-Hexa-2,4-dienedioic acid mono-((E)-4-methoxycarbonyl-3-methyl-but-3-enyl) ester (80514-96-1)

Guidance literature:

With potassium tert-butylate; In diethyl ether; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)87334-7

Reference yield:

5-hydroxy-3-methyl-2-(E)-pentenoic acid methyl ester (35066-36-5) → (2E,4Z)-Hexa-2,4-dienedioic acid mono-((E)-4-methoxycarbonyl-3-methyl-but-3-enyl) ester (80514-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / pyridine / tetrahydrofuran / 0.5 h / 0 °C

2: 81 percent / 1 h / 100 °C

3: 1.) NaH / 1.) THF, 0 deg C, 20 min, 2.) from 0 deg C to room temp., 1 h

With pyridine; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo00345a005

Reference yield:

methyl 3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate (35066-33-2,35066-34-3) → (2E,4Z)-Hexa-2,4-dienedioic acid mono-((E)-4-methoxycarbonyl-3-methyl-but-3-enyl) ester (80514-96-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / 2 M HCl / methanol / 1 h / Ambient temperature

2: 88 percent / pyridine / tetrahydrofuran / 0.5 h / 0 °C

3: 81 percent / 1 h / 100 °C

4: 1.) NaH / 1.) THF, 0 deg C, 20 min, 2.) from 0 deg C to room temp., 1 h

With pyridine; hydrogenchloride; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo00345a005

upstream raw materials:

5-hydroxy-2-(5H)-furanone

methyl (E)-3-methyl-5-<(di-O-methylphosphono)acetoxy>pent-2-enoate

5-hydroxy-3-methyl-2-(E)-pentenoic acid methyl ester

methyl (E)-5-(2-bromoacetoxy)-3-methylpent-2-enoate

Refernces

• 1、 White,Carter,Kezar III. "Stereoselective synthesis of the macrocycle segment of verrucarin J". . p. 929 - 932. Retrieved 2007/10/02.