Dehydropipernonaline

Base Information

• Chemical Name: Dehydropipernonaline
• CAS No.: 107584-38-3
• Molecular Formula: C₂₁H₂₅NO₃
• Molecular Weight: 339.434
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID401315333
• Nikkaji Number: J2.471.186B
• Wikidata: Q76386734
• Metabolomics Workbench ID: 49170
• ChEMBL ID: CHEMBL483708
• Mol file: 107584-38-3.mol

Synonyms:dehydropipernonaline;N-(9-(3,4-methylenedioxyphenyl)-2,4,8-nonatrienoyl)piperidine

Chemical Property of Dehydropipernonaline

Chemical Property:

• Vapor Pressure: 1.52E-13mmHg at 25°C
• Boiling Point: 582.2°Cat760mmHg
• Flash Point: 305.9°C
• PSA: 38.77000
• Density: 1.15g/cm³
• LogP: 4.27150
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 339.18344366
• Heavy Atom Count: 25
• Complexity: 505

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)C(=O)C=CC=CCCC=CC2=CC3=C(C=C2)OCO3
• Isomeric SMILES: C1CCN(CC1)C(=O)/C=C/C=C/CC/C=C/C2=CC3=C(C=C2)OCO3

Technology Process of Dehydropipernonaline

There total 7 articles about Dehydropipernonaline 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%

piperidine (110-89-4) + (2E,4E,8E)-9-benzo[1,3]dioxol-5-yl-nona-2,4,8-trienoic acid ethyl ester (177555-26-9) → Dehydropipernonaline (107584-38-3)

Guidance literature:

With bis(bis(trimethylsilyl)amido)tin(II); In hexane; for 12h; Ambient temperature;

DOI:10.1139/v96-046

Reference yield:

piperonal (120-57-0,30024-74-9) → Dehydropipernonaline (107584-38-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) boron trifluoride etherate / 1.) THF, 0 deg C; 0 deg C to RT, 70 min; 2.) THF, RT, 14 h

2: 1.) LAH; 2.) NaOH, water / tetrahydrofuran / 1.) 0 deg C to RT, 3.5 h; 2.) RT, 20 min

3: 91 percent / triphenylphosphine, imidazole, iodine / diethyl ether; acetonitrile / 14 h / Ambient temperature

4: 93 percent / dimethylsulfoxide / 2 h / 8 °C

5: 79 percent / n-butyllithium / tetrahydrofuran; hexane / 1.5 h / 0 °C

6: 84 percent / glacial acetic acid, triphenylphosphine / toluene / 48 h / Heating

7: 88 percent / SN2 / hexane / 12 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; water; iodine; bis(bis(trimethylsilyl)amido)tin(II); acetic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1139/v96-046

Reference yield:

1-iodo-6-(3',4'-methylenedioxyphenyl)-5E-hexene (107022-82-2) → Dehydropipernonaline (107584-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / dimethylsulfoxide / 2 h / 8 °C

2: 79 percent / n-butyllithium / tetrahydrofuran; hexane / 1.5 h / 0 °C

3: 84 percent / glacial acetic acid, triphenylphosphine / toluene / 48 h / Heating

4: 88 percent / SN2 / hexane / 12 h / Ambient temperature

With n-butyllithium; bis(bis(trimethylsilyl)amido)tin(II); acetic acid; triphenylphosphine; In tetrahydrofuran; hexane; dimethyl sulfoxide; toluene;

DOI:10.1139/v96-046

upstream raw materials:

piperidine

(2E,4E,8E)-9-benzo[1,3]dioxol-5-yl-nona-2,4,8-trienoic acid ethyl ester

piperonal

1-iodo-6-(3',4'-methylenedioxyphenyl)-5E-hexene

Refernces