2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)-

Base Information

• Chemical Name: 2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)-
• CAS No.: 80515-01-1
• Molecular Formula: C₁₁H₁₉O₇P
• Molecular Weight: 294.241
• Mol file: 80515-01-1.mol

Synonyms:2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)-;80515-01-1

Chemical Property of 2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)-

Chemical Property:

• Vapor Pressure: 2.36E-06mmHg at 25°C
• Boiling Point: 392.1°C at 760 mmHg
• Flash Point: 204.4°C
• Density: 1.189g/cm³
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 294.08683994
• Heavy Atom Count: 19
• Complexity: 381

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)-

There total 4 articles about 2-Pentenoic acid, 5-(((dimethoxyphosphinyl)acetyl)oxy)-3-methyl-, methyl ester, (E)- 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: 81.0%

methyl (E)-5-(2-bromoacetoxy)-3-methylpent-2-enoate (80515-00-0) + phosphorous acid trimethyl ester (121-45-9) → methyl (E)-3-methyl-5-<(di-O-methylphosphono)acetoxy>pent-2-enoate (80515-01-1)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1021/jo00345a005

Reference yield:

5-hydroxy-3-methyl-2-(E)-pentenoic acid methyl ester (35066-36-5) → methyl (E)-3-methyl-5-<(di-O-methylphosphono)acetoxy>pent-2-enoate (80515-01-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 81 percent / 1 h / 100 °C

With pyridine; In tetrahydrofuran;

DOI:10.1021/jo00345a005

Reference yield:

methyl 3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate (35066-33-2,35066-34-3) → methyl (E)-3-methyl-5-<(di-O-methylphosphono)acetoxy>pent-2-enoate (80515-01-1)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1021/jo00345a005

upstream raw materials:

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

2-Bromoacetyl bromide

phosphorous acid trimethyl ester

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

Downstream raw materials:

(2E,4Z)-Hexa-2,4-dienedioic acid mono-((E)-4-methoxycarbonyl-3-methyl-but-3-enyl) ester

Refernces

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