5-Methyl-2-propyldecahydroquinoline

Base Information

• Chemical Name: 5-Methyl-2-propyldecahydroquinoline
• CAS No.: 27766-71-8
• Molecular Formula: C₁₃H₂₅N
• Molecular Weight: 195.348
• DSSTox Substance ID: DTXSID60950451
• Nikkaji Number: J17.296K
• Wikidata: Q82928520
• Mol file: 27766-71-8.mol

Synonyms:(+,-)-2-epi-pumiliotoxin C;5-methyl-2-propyldecahydroquinoline;decahydro-5-methyl-2-propyl-quinoline;decahydro-5-methyl-2-propylquinoline;pumiliotoxin C

Chemical Property of 5-Methyl-2-propyldecahydroquinoline

Chemical Property:

• Vapor Pressure: 0.0116mmHg at 25°C
• Boiling Point: 261.4°Cat760mmHg
• Flash Point: 110.8°C
• PSA: 12.03000
• Density: 0.854g/cm³
• LogP: 3.67210
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 195.198699802
• Heavy Atom Count: 14
• Complexity: 178

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1CCC2C(CCCC2N1)C
• Isomeric SMILES: CCC[C@H]1CC[C@H]2[C@@H](CCC[C@H]2N1)C

Technology Process of 5-Methyl-2-propyldecahydroquinoline

There total 127 articles about 5-Methyl-2-propyldecahydroquinoline 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: 98.0%

(2S,4aR,5R)-5-Methyl-2-propyl-1,2,4a,5,6,7,8,8a-octahydro-quinoline (115094-16-1,115094-17-2) → (-)-8a-epipumiliotoxin c (27766-71-8,55785-29-0,57458-05-6,63107-18-6,87037-30-7,87144-83-0,106565-72-4,115182-14-4,142128-49-2,145373-85-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 0.5h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00251a002

Reference yield: 92.0%

(2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline (160798-33-4) → (-)-pumiliotoxin C (27766-71-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/0040-4039(94)88469-2

Reference yield: 88.0%

(rac)-(2R,4aS,5R,8aS)-1-benzyl-5-methyl-2-propyl-decahydroquinoline (61475-92-1,87037-31-8,87037-32-9) → (rac)-(2R,4aS,5R,8aS)-5-methyl-2-propyl-decahydroquinoline (27766-71-8,55785-29-0,57458-05-6,63107-18-6,87037-30-7,87144-83-0,106565-72-4,115182-14-4,142128-49-2,145373-85-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 16h;

DOI:10.1055/s-2004-834904

upstream raw materials:

(S)-8-Methyl-3-phenyl-5-propyl-decahydro-oxazolo[2,3-j]quinoline

(2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

(2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline

(2S,4aS,5R,8aR)-5-Methyl-2-propyl-octahydro-quinoline-1-carboxylic acid benzyl ester

Downstream raw materials:

(2R^*,4aS^*,5S^*,8aR^*)-2-(1-propyl)-5-methyldecahydroquinoline hydrochloride

Refernces

Ruthenium-Catalyzed Hydration of Nitriles and Transformation of δ-Ketonitriles to Ene-lactams: Total Synthesis of (-)-Pumiliotoxin C

10.1016/S0040-4020(01)81902-5

The study explores the efficient hydration of nitriles using the RuH2(PPh3)4 catalyst, converting them into corresponding amides under neutral conditions with only 1-2 equivalents of water. This method is advantageous due to its simplicity, high efficiency, and mild reaction conditions. The study extends this principle to transform ?-ketonitriles into ene-lactams, which are versatile intermediates for synthesizing piperidine and hydroquinoline ring systems. The efficiency of these reactions is demonstrated through the short-step synthesis of (-)-pumiliotoxin C, a toxic skin alkaloid produced by Central American frogs. The study also investigates the catalytic activities of various metal complexes in these transformations, finding RuH2(PPh3)4 to be the most effective. Additionally, the study explores the conversion of ene-lactams into ?-dioxylactams and further into ?-substituted lactams using different nucleophiles in the presence of TiCl4, providing a useful method for the stereoselective synthesis of cyclic amines.

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: Synthesis of (±)-2-epi-pumiliotoxin C

10.1021/jo902172r

The research focuses on the synthesis of (+-)-2-epi-pumiliotoxin C using oxazolone cycloadducts as heterocyclic scaffolds. The study employs an intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene to directly access the functionalized octahydroquinoline framework. Key chemicals involved in the research include divinyl carbinol, heptadienal, oxazolidine-2,4-dione, and diethylzinc. The synthesis process involves several steps, such as Saucy-type rearrangement, Grignard reaction, Mitsunobu reaction, cyclopropanation, and hydrogenolysis, ultimately leading to the final product (+-)-2-epi-pumiliotoxin C. The research demonstrates the utility of oxazolone IMDA cycloadducts as valuable scaffolds for alkaloid construction and provides a direct incorporation approach to synthesizing complex natural products.