Piperovatine

Base Information

• Chemical Name: Piperovatine
• CAS No.: 25090-18-0
• Molecular Formula: C17H23 N O2
• Molecular Weight: 273.375
• Hs Code.: 2924299090
• Nikkaji Number: J17.738E
• Metabolomics Workbench ID: 129462
• ChEMBL ID: CHEMBL250442
• Mol file: 25090-18-0.mol

Synonyms:N-isobutyl-6-(4-methoxyphenyl)sorbamide;piperovatine

Chemical Property of Piperovatine

Chemical Property:

• Vapor Pressure: 3.5E-09mmHg at 25°C
• Melting Point: 115-119 °C
• Boiling Point: 474.8°Cat760mmHg
• PKA: 14?+-.0.46(Predicted)
• Flash Point: 241°C
• PSA: 41.82000
• Density: 1.005g/cm³
• LogP: 3.96260
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 273.172878976
• Heavy Atom Count: 20
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CNC(=O)C=CC=CCC1=CC=C(C=C1)OC
• Isomeric SMILES: CC(C)CNC(=O)/C=C/C=C/CC1=CC=C(C=C1)OC
• Description: This alkaloid was first isolated from Piper ovaturn and assigned the empirical formula C16H2102N, later changed to that given above by Price and Pinder who also discover the base in Ottonia vehlii Kth. The alkaloid crystallizes from Et20 in colourless needles and has an ultraviolet spectrum containing a single broad absorption maximum at 262 mil. In the unsaturated side chain, both of the double bonds are trans. According to Cash, the alkaloid is a temporary depressant of motor and sensory nerve fibres and of sensory nerve endings. It has the effect of a heart poison and also as a spinal cord stimulant in frogs bringing about a tonic spasm somewhat similar to that induced by strychnine.

Technology Process of Piperovatine

There total 19 articles about Piperovatine 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:

para-iodoanisole (696-62-8) → piperovatine (25090-18-0)

Guidance literature:

Multi-step reaction with 6 steps

1: CuI / (Ph₃P)2PdCl₂ / triethylamine

2: 1.) H₂; 2.) NEt₃ / 1.) Pd/C / 1.) EtOAc; 2.) DMSO, CH₂Cl₂

3: piperidine / acetonitrile

4: DMAP / pyridine

5: 73 percent / bis-trimethylsilylacetamide / Mo(CO)6 / toluene

6: 1.) aq. HCl; 2.) phenyl N-phenylphosphoramidochloridate, NEt₃ / 1.) dioxane; 2.) CH₂Cl₂

With piperidine; hydrogenchloride; dmap; copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; triethylamine; Phenyl N-phenylphosphoramidochloridate; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; hexacarbonyl molybdenum; In pyridine; triethylamine; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)84756-5

Reference yield:

4-(p-methoxyphenyl)-3-butyn-1-ol (52999-15-2) → piperovatine (25090-18-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂; 2.) NEt₃ / 1.) Pd/C / 1.) EtOAc; 2.) DMSO, CH₂Cl₂

2: piperidine / acetonitrile

3: DMAP / pyridine

4: 73 percent / bis-trimethylsilylacetamide / Mo(CO)6 / toluene

5: 1.) aq. HCl; 2.) phenyl N-phenylphosphoramidochloridate, NEt₃ / 1.) dioxane; 2.) CH₂Cl₂

With piperidine; hydrogenchloride; dmap; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; triethylamine; Phenyl N-phenylphosphoramidochloridate; palladium on activated charcoal; hexacarbonyl molybdenum; In pyridine; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)84756-5

Reference yield:

4-(4-methoxyphenyl)butyraldehyde (56047-51-9) → piperovatine (25090-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: piperidine / acetonitrile

2: DMAP / pyridine

3: 73 percent / bis-trimethylsilylacetamide / Mo(CO)6 / toluene

4: 1.) aq. HCl; 2.) phenyl N-phenylphosphoramidochloridate, NEt₃ / 1.) dioxane; 2.) CH₂Cl₂

With piperidine; hydrogenchloride; dmap; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; Phenyl N-phenylphosphoramidochloridate; hexacarbonyl molybdenum; In pyridine; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)84756-5

upstream raw materials:

6-(p-Methoxyphenyl)-hexa-trans-2-trans-4-diensaeure

isobutylamine

3-(4-methoxyphenyl)prop-1-yne

(E)-N-(2-methylpropyl)-3-iodoacrylamide

Downstream raw materials:

N-isobutyl-6-(p-methoxyphenyl)hexa-3,5-dienamide