(2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol

Base Information

• Chemical Name: (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol
• CAS No.: 129785-16-6
• Molecular Formula: C₉H₁₉NO
• Molecular Weight: 157.256
• Mol file: 129785-16-6.mol

Synonyms:2-Piperidineethanol,a,6-dimethyl-, [2R-[2a(R*),6a]]-; (-)-Pinidinol; Pinidinol

Chemical Property of (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol

Chemical Property:

• Vapor Pressure: 0.00285mmHg at 25°C
• Boiling Point: 253.3°Cat760mmHg
• Flash Point: 88°C
• Density: 0.901g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol, also known as (-)-pinidinol, is a toxic piperidine alkaloid found in pine and spruce trees, notably in *Pinus jeffreyi*. It is characterized by its presence in the nonvolatile fraction of tree extracts and contributes to the teratogenic effects observed in livestock, such as pine needle abortion in pregnant cows. (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol's structure and biosynthetic pathway suggest it forms through piperidine ring modifications, highlighting its ecological and toxicological significance.

Technology Process of (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol

There total 34 articles about (2R)-1-[(2R,6R)-6-methylpiperidin-2-yl]propan-2-ol 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: 97.0%

[(E)-(1R,7R)-7-hydroxy-1-methyl-5-oxo-oct-3-enyl]-carbamic acid benzyl ester (913986-11-5) → (-)-pinidinol (55267-91-9,55331-42-5,55331-44-7,129785-16-6,150134-95-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3h; under 760.051 Torr;

DOI:10.3987/com-06-10847

Reference yield: 89.0%

C15H33NOSi (913986-13-7) → (-)-pinidinol (55267-91-9,55331-42-5,55331-44-7,129785-16-6,150134-95-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.3987/com-06-10847

Reference yield: 66.0%

(2R,6R)-2-((R)-2-Hydroxy-propyl)-6-methyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester (217823-97-7) → (-)-pinidinol (55267-91-9,55331-42-5,55331-44-7,129785-16-6,150134-95-5)

Guidance literature:

With 10% Cd/Pd; ammonium acetate; In tetrahydrofuran; for 12h;

DOI:10.1016/S0040-4020(98)00831-X

upstream raw materials:

(+)-1,2-Dehydropinidinol

(2R,6R)-2-((R)-2-Hydroxy-propyl)-6-methyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester

(2R,2'R,6'R)-(-)-1-(6'-methylpiperidin-2'-yl)-2-(tert-butyldiphenylsilyloxy)propane

[(E)-(1R,7R)-7-hydroxy-1-methyl-5-oxo-oct-3-enyl]-carbamic acid benzyl ester

Refernces

Toxic Piperidine Alkaloids from Pine (Pinus) and Spruce (Picea) Trees. New Structures and a Biosynthetic Hypothesis

10.1021/jo00070a014

The research investigates the presence and structure of toxic piperidine alkaloids in various species of pine and spruce trees. The study aims to identify new alkaloids, understand their biosynthetic pathways, and explore their potential toxicity, particularly in relation to the pine needle abortion phenomenon observed in pregnant cows. Key chemicals identified include cis- and trans-disubstituted piperidines, with specific compounds such as (-)-pinidinol, (+)-6-epidihydropinidine, (-)-pinidinone, and (+)-1,2-dehydropinidinol. (-)-pinidinol (3) is characterized by its presence in the nonvolatile fraction of the extracts and is notable for its significant concentration in species such as P. jeffreyi, even though it had not been previously reported in this conifer. The research employs techniques like GCMS analysis, NMR spectroscopy, and X-ray crystallography to characterize these compounds. The findings suggest a plausible biosynthetic scheme for these alkaloids, indicating that piperidine ring formation occurs before side-chain modifications. The study concludes that certain alkaloids, particularly from Ponderosa pine, exhibit high teratogenicity, potentially explaining the pine needle abortion issue. Future work may involve further exploration of the ecological roles of these alkaloids and their impact on herbivores.