6035-31-0

Basic information

• Product Name: α,α'-(2,6-Piperidinediyl)bis(acetophenone)
• Synonyms: Isolobelanine;Norlobelanine;α,α'-(2,6-Piperidinediyl)bis(acetophenone)
• CAS NO: 6035-31-0
• Molecular Formula: C₂₁H₂₃NO₂
• Molecular Weight: 321.41282
• Mol File: 6035-31-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 120-121°
• Boiling Point: 484.1±10.0 °C(Predicted)
• Appearance: /
• Density: 1.084±0.06 g/cm3(Predicted)
• PKA: 9.05±0.10(Predicted)
• CAS DataBase Reference: α,α'-(2,6-Piperidinediyl)bis(acetophenone)(CAS DataBase Reference)
• NIST Chemistry Reference: α,α'-(2,6-Piperidinediyl)bis(acetophenone)(6035-31-0)
• EPA Substance Registry System: α,α'-(2,6-Piperidinediyl)bis(acetophenone)(6035-31-0)

Safety Data

• Hazardous Substances Data: 6035-31-0(Hazardous Substances Data)

Usage

Description

α,α'-(2,6-Piperidinediyl)bis(acetophenone) is an organic compound with the molecular formula C18H26N2O2. It is an alkaloid derived from Lobelia inflata Linn and L. sessiliflora, initially designated as isolobelanine but later identified as norlobelanine. α,α'-(2,6-Piperidinediyl)bis(acetophenone) forms well-crystallized salts, including the hydrochloride, nitrate, methiodide, and N-benzoyl derivatives.

Uses

1. Used in Pharmaceutical Industry:
α,α'-(2,6-Piperidinediyl)bis(acetophenone) is used as an active pharmaceutical ingredient for its potential therapeutic effects. α,α'-(2,6-Piperidinediyl)bis(acetophenone) has been shown to have various biological activities, making it a promising candidate for the development of new drugs.
2. Used in Chemical Research:
As an alkaloid with unique structural properties, α,α'-(2,6-Piperidinediyl)bis(acetophenone) is used as a subject of study in chemical research. Researchers can explore its chemical behavior, interactions with other compounds, and potential applications in the synthesis of new molecules.
3. Used in Analytical Chemistry:
The well-crystallized salts of α,α'-(2,6-Piperidinediyl)bis(acetophenone) can be utilized in analytical chemistry for the identification and quantification of the compound in various samples. The distinct melting points of its salts can be helpful in characterizing and differentiating it from other similar compounds.
4. Used in Drug Synthesis:
α,α'-(2,6-Piperidinediyl)bis(acetophenone) can be used as a starting material or intermediate in the synthesis of other pharmaceutically active molecules. Its unique structure and reactivity make it a valuable component in the development of new drugs with potential applications in various therapeutic areas.

References

Wieland, Hermsen., Annalen, 444, 63 (1926)Wieland, Drishaus., ibid, 473, 117 (1929)Wieland, Koschkara, Dane., ibid, 473, 118 (1929)Wieland, Koschkara., ibid, 473, 122 (1929)

Upstream product

• 614-20-0 3-oxo-3-phenylpropionic acid 
• 111-30-8 Glutaraldehyde 
• 102319-42-6 1,9-diphenylnona-2,7-diene-1,9-dione 
• 141-78-6 ethyl acetate 
• 495-50-1 2,2′-(piperidine-2,6-trans-diyl)bis(1-phenylethanone) 

Downstream Products

• 98-86-2 acetophenone 

Relevant articles and documents

Thermodynamic epimeric equilibration and crystallisation-induced dynamic resolution of lobelanine, norlobelanine and related analogues

The step-economical synthesis of lobelanine involving a ring closing double aza-Michael (RCDAM) reaction is revisited and successfully extended to the synthesis of various configurationally more stable analogues. Owing to the presence of a configurationally labile β-aminoketone subunit, lobelanine is prone to self-catalyze mutarotation in solution. Through the synthesis of original lobelanine analogues, we studied the influence of (i) the size of the central heterocycle, (ii) the bulkiness of the nitrogen protecting group, and (iii) the phenacyl arm substituent on the thermodynamic equilibrium and its displacement by crystallisation-induced dynamic resolution (CIDR). We demonstrated that fine structural tuning combined with optimized CIDR conditions favours the first efficient diastereoselective synthesis of lobelanine's analogues.