125356-66-3

Basic information

• Product Name: 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol
• Synonyms: (2S)-1-Methyl-5β-nonyl-2β-benzylpyrrolidin-3β-ol;1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol;Preussine
• CAS NO: 125356-66-3
• Molecular Formula: C₂₁H₃₅NO
• Molecular Weight: 317.5087
• Mol File: 125356-66-3.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 432.1°Cat760mmHg
• Flash Point: 11.1°C
• Appearance: /
• Density: 0.967g/cm³
• Vapor Pressure: 3.1E-08mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol(125356-66-3)
• EPA Substance Registry System: 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol(125356-66-3)

Safety Data

• Hazardous Substances Data: 125356-66-3(Hazardous Substances Data)

Usage

Description

1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol is a complex organic compound that belongs to the class of pyrrolidine derivatives. It features a pyrrolidine ring with a methyl group at the 1 position, a benzyl group at the 2β position, and a nonyl group at the 5β position, along with a hydroxyl group attached to the 3β position. This unique structure endows it with potential biological activities and applications, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol is used as a pharmaceutical compound for its potential biological activities. Its unique structure suggests that it may have therapeutic properties that could be harnessed for the development of new drugs. However, further research and studies are required to fully understand its properties and to explore its potential uses in treating various medical conditions.
Note: Since the provided materials do not specify particular applications or industries for 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol beyond the general mention of the pharmaceutical industry, the uses listed are broad and based on the potential inferred from its classification as a pyrrolidine derivative with a complex structure. More detailed applications would require additional information or research findings.

InChI:InChI=1/C21H35NO/c1-3-4-5-6-7-8-12-15-19-17-21(23)20(22(19)2)16-18-13-10-9-11-14-18/h9-11,13-14,19-21,23H,3-8,12,15-17H2,1-2H3/t19-,20+,21+/m1/s1

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Relevant articles and documents

Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity

Short syntheses of oxa-preussin, racemic preussin and (-)-preussin are reported. Starting from a racemic 3-nonyl-substituted methoxyallene derivative, its lithiation and addition to phenylethanal provided the corresponding allenyl alcohol that was converted into two diastereomeric dihydrofuran derivatives by silver nitrate-catalyzed 5-endo-trig cyclization. The acid hydrolysis of the enol ether moiety gave heterocyclic ketones and subsequent highly stereoselective reductions with l-selectride furnished 2-benzyl-5-nonylfuran-3-ol derivatives in good overall yield. The major all-cis-diastereomer has the skeleton and relative configuration of preussin and is hence called oxa-preussin. An analogous sequence with the same allene, but an N-sulfonyl imine as the electrophile, finally led to racemic preussin. The stereoselectivities of the individual steps are discussed in detail. With an enantiopure 2-benzyl-5-nonylpyrrolidin-3-one intermediate the preparation of (-)-preussin with an enantiomeric ratio of >95:5 could be accomplished in a few steps. The sign of the optical rotation of this product finally proved the absolute configurations of its precursors and demonstrated that our chiral auxiliary-based route led to the antipode of the natural product. The cytotoxicity of several of the prepared heterocycles against MCF-7 tumor cells was investigated and five compounds, including racemic and enantiopure (-)-preussin, were identified as highly cytotoxic with IC50 values in the range of 3-6 μM.

Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations

Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.

A concise and stereoselective synthesis of hydroxypyrrolidines: Rapid synthesis of (+)-preussin

A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of β-iminochlorohydrins, which are readily available from β- ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.