3-(3,4-Dimethyl-2-pentenoyl)bruceantin

Base Information

• Chemical Name: 3-(3,4-Dimethyl-2-pentenoyl)bruceantin
• CAS No.: 76215-40-2
• Molecular Formula: C₃₄H₄₄O₁₂
• Molecular Weight: 644.716
• Mol file: 76215-40-2.mol

Synonyms:3-(3,4-Dimethyl-2-pentenoyl)bruceantin;76215-40-2;Picras-3-en-21-oic acid, 3,15-bis((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-11,12-dihydroxy-2,16-dioxo-, methyl ester, (3(E),11beta,12alpha,15beta(E))-;C35H36O12;C35-H36-O12

Chemical Property of 3-(3,4-Dimethyl-2-pentenoyl)bruceantin

Chemical Property:

• Vapor Pressure: 2.33E-28mmHg at 25°C
• Boiling Point: 783.5°C at 760 mmHg
• Flash Point: 241.6°C
• Density: 1.31g/cm³
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 658.29892690
• Heavy Atom Count: 47
• Complexity: 1490

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)OC(=O)C=C(C)C(C)C
• Isomeric SMILES: CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3C45[C@@H]2[C@H]([C@@H]([C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)OC(=O)/C=C(\C)/C(C)C

Technology Process of 3-(3,4-Dimethyl-2-pentenoyl)bruceantin

There total 8 articles about 3-(3,4-Dimethyl-2-pentenoyl)bruceantin 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: 77.0%

3-(3,4-dimethyl-2-pentenoyl)bruceolide (76215-41-3) + (E)-3,4-dimethylpent-4-enoyl chloride (76215-43-5) → 3,15-bis(3,4-dimethyl-2-pentenoyl)bruceolide (76215-40-2)

Guidance literature:

With pyridine; In chloroform; at 50 ℃; for 23h;

DOI:10.1021/jo00319a019

Reference yield: 47.0%

bruceolide + (E)-3,4-dimethylpent-4-enoyl chloride (76215-43-5) → 3-(3,4-dimethyl-2-pentenoyl)bruceolide (76215-41-3) + 3,15-bis(3,4-dimethyl-2-pentenoyl)bruceolide (76215-40-2)

Guidance literature:

With pyridine; In chloroform; at 56 ℃; for 24h;

DOI:10.1021/jo00319a019

Reference yield:

3-methyl-butan-2-one (563-80-4) → 3,15-bis(3,4-dimethyl-2-pentenoyl)bruceolide (76215-40-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.)sodium hydride / 1.)diglyme, 0 deg C_., 30 min, 2.) 3 h.

2: 91 percent / 0.5 N KOH / H₂O / 17 h / 80 °C

3: thionyl chloride / benzene / Heating

4: 31 percent / pyridine / CHCl₃ / 24 h / 56 °C

5: 77 percent / pyridine / CHCl₃ / 23 h / 50 °C

With pyridine; potassium hydroxide; thionyl chloride; sodium hydride; In chloroform; water; benzene;

DOI:10.1021/jo00319a019

upstream raw materials:

(E)-3,4-dimethylpent-4-enoyl chloride

3-(3,4-dimethyl-2-pentenoyl)bruceolide

3-methyl-butan-2-one

ethyl (E)-3,4-dimethyl-2-pentenoate