Epilachnadiene

Base Information

• Chemical Name: Epilachnadiene
• CAS No.: 147363-83-5
• Molecular Formula: C₁₆H₂₇NO₂
• Molecular Weight: 265.396
• Nikkaji Number: J792.117I
• Wikidata: Q105101746
• Mol file: 147363-83-5.mol

Synonyms:11-propyl-12-azacyclotetradec-5,8-dien-14-olide;epilachnadiene

Chemical Property of Epilachnadiene

Chemical Property:

• Vapor Pressure: 3.89E-07mmHg at 25°C
• Boiling Point: 416.2°C at 760 mmHg
• PKA: 8.78±0.40(Predicted)
• Flash Point: 205.5°C
• PSA: 38.33000
• Density: 0.914g/cm³
• LogP: 3.69320
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 265.204179104
• Heavy Atom Count: 19
• Complexity: 297

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1CC=CCC=CCCCC(=O)OCCN1
• Isomeric SMILES: CCC[C@@H]1C/C=C\C/C=C\CCCC(=O)OCCN1

Technology Process of Epilachnadiene

There total 29 articles about Epilachnadiene 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: 90.0%

(7Z,10Z)-15-Oxo-5-propyl-1-oxa-4-aza-cyclopentadeca-7,10-diene-4-carboxylic acid tert-butyl ester (161496-75-9) → (+/-)-epilachnadiene (147363-83-5)

Guidance literature:

With trifluoroacetic acid; In neat (no solvent); for 0.5h; Ambient temperature;

DOI:10.1016/0040-4039(94)02197-J

Reference yield: 90.0%

(7Z,10Z)-(R)-15-Oxo-5-propyl-1-oxa-4-aza-cyclopentadeca-7,10-diene-4-carboxylic acid tert-butyl ester (185421-93-6) → (7Z,10Z)-(R)-5-Propyl-1-oxa-4-aza-cyclopentadeca-7,10-dien-15-one (147363-83-5)

Guidance literature:

With trifluoroacetic acid; for 0.25h; Ambient temperature;

DOI:10.1016/0040-4039(96)01960-0

Reference yield:

(2S,3S)-3-propyl-2-oxiranemethanol (89321-71-1) → (7Z,10Z)-(R)-5-Propyl-1-oxa-4-aza-cyclopentadeca-7,10-dien-15-one (147363-83-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 72 percent / PPh₃, CCl₄, NaHCO₃ / 3 h / Heating

2: 70 percent / LiNH₂ / tetrahydrofuran / 6 h / -30 °C

3: 65 percent / NaNH₂, diaminopropane / 2 h / 80 °C

4: 1.) EtMgBr, 2.) CuCl / 1.) THF, 2.) THF

5: 86 percent / H₂ / Pd/CaCO₃ / methanol / 3 h

6: NEt₃ / CH₂Cl₂ / 3 h / 0 °C

7: 8 h / 80 °C

8: 75 percent / NEt₃ / CH₂Cl₂ / 3 h / Ambient temperature

9: 95 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

10: 82 percent / PPTS / ethanol / 4 h / Heating

11: PCC, celite / CH₂Cl₂ / 3 h

12: Ag₂O, NaOH, H₂O / ethanol / 4 h / Ambient temperature

13: NEt₃ / tetrahydrofuran / 2 h / Ambient temperature

14: 78 percent / DMAP / toluene / 12 h / 90 °C

15: 90 percent / TFA / 0.25 h / Ambient temperature

With tetrachloromethane; dmap; sodium hydroxide; lithium amide; Celite; ethylmagnesium bromide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; sodium amide; Trimethylenediamine; triethylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; copper(l) chloride; silver(l) oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/0040-4039(96)01960-0

upstream raw materials:

(7Z,10Z)-15-Oxo-5-propyl-1-oxa-4-aza-cyclopentadeca-7,10-diene-4-carboxylic acid tert-butyl ester

7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol

2-(7-Bromo-hept-5-ynyloxy)-tetrahydro-pyran

Methanesulfonic acid 7-(tetrahydro-pyran-2-yloxy)-hept-2-ynyl ester

Refernces

• 1、 Venkateswara Rao,Satish Kumar. "Synthesis of azamacrolides - (±)epilachnadiene, (±)norepilachnene and (±)homoepilachnene". . p. 147 - 150. Retrieved 2007/10/02.