Methylisopelletierine

Base Information

• Chemical Name: Methylisopelletierine
• CAS No.: 18747-42-7
• Molecular Formula: C9H17NO
• Molecular Weight: 155.24
• UNII: 7A42OMR1WL
• DSSTox Substance ID: DTXSID30940208
• Nikkaji Number: J505.929A
• Wikidata: Q27107473
• Metabolomics Workbench ID: 44330
• Mol file: 18747-42-7.mol

Synonyms:Methylisopelletierine;18747-42-7;1-(1-methylpiperidin-2-yl)propan-2-one;N-Methylisopelletierine;1-(1-Methyl-2-piperidinyl)acetone;Methylisopunicine;(+/-)-N-Methylpelletierine;(+/-)-1-Methylpelletierine;N-Methylpelletierine, (+/-)-;7A42OMR1WL;2-Propanone, 1-(1-methyl-2-piperidinyl)-;N-Methylpelletierine;(1-Methyl-2-piperidyl)acetone;UNII-7A42OMR1WL;Methylpelletierine;Methyl-isopelletierin;C06184;a-N-Methylpelletierin-b-one;CHEBI:7321;NIOSH/AL6480000;SCHEMBL14430402;DTXSID30940208;TYHJMEIBGDDCPA-UHFFFAOYSA-N;HY-N3262;Acetone, (1-methyl-2-piperidyl)-;AKOS000278131;AKOS017341561;1-(1-Methyl-2-piperidinyl)acetone #;2-Propanone, (1-methyl-2-piperidinyl)-;AL64800000;CS-0023739;EN300-365095;()-N-Methylpelletierine;Q27107473;2-Propanone, 1-(1-methyl-2-piperidinyl)-, (.+/-.)-

Chemical Property of Methylisopelletierine

Chemical Property:

• Vapor Pressure: 0.137mmHg at 25°C
• Refractive Index: 1.449
• Boiling Point: 216.9 °C at 760 mmHg
• PKA: 9.53±0.10(Predicted)
• Flash Point: 66.9 °C
• PSA: 20.31000
• Density: 0.92 g/cm³
• LogP: 1.38770
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 155.131014166
• Heavy Atom Count: 11
• Complexity: 145

Purity/Quality:

98%min ^*data from raw suppliers

Methylisopelletierine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC1CCCCN1C
• Description: This alkaloid occurs in the bark of Punica Granatum L. and was first isolated by Piccinini under the name of isomethylpelletierine. The base is an oily liquid with an alkaline reaction, miscible with H20 and optically inactive. The hydrochloride has m.p. lS6°C; the hydrobromide, m.p. lSI-2°C; the aurichloride forms rosettes of orange-yellow needles, m.p. lIS-7°C and the picrate has m.p. lS7-8°C. The alkaloid may be resolved into its optically active components. (+)-methy1isopelletierine (+)-hydrogen tartrate has m.p. 133-4°C; [α]20D + 22.7°, the corresponding figures for the antipode being m.p. 132-40c;~aH)S - 20.83° while the two hydrochlorides have [α]18D + 11.08° and - 10.64° respectively.The base gives a semicarbazone as colourless crystals, m.p. 169°C; an oxime, b.p. 1600C/12 mm and a hydrazone, b.p. lS4-SoC/29 mm. The methiodide yields cubic crystals, m.p. lS6°C. Oxidation with chromic acid in H2S04 furnishes N-methylpiperidine-2-carboxylic acid.

Technology Process of Methylisopelletierine

There total 19 articles about Methylisopelletierine 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: 34.0%

1-(1-methylpiperidin-2-yl)prop-1-yne (51498-57-8) → ethyl 1-methylpiperidin-2-yl ketone (125039-04-5) + N-methylpelletierine (18747-42-7)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; Heating;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + isopelletierine (4396-01-4) → N-methylpelletierine (18747-42-7)

Guidance literature:

With formic acid; at 100 ℃; for 6h;

DOI:10.1016/S0031-9422(00)97554-X

Reference yield:

1-methylpiperidine-2-thione (13070-07-0) → N-methylpelletierine (18747-42-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 6 h / Ambient temperature

2: 1) BuLi / 1) hexane, THF, 2) THF, -78 deg C

3: 1) LiAlH₄, 2) 10percent aq. NaOH / 1) -20 deg C, 2 h, THF, hexane, 2) -10 deg C, 1 h, THF, hexane

4: 1) bis(1,2-dimethylpropyl)borane, 2) 6M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, 5 deg C, overnight, 2) THF, r.t., 1 h

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran;

upstream raw materials:

2-acetonylpyridine

dimethyl sulfate

acetonedicarboxylic acid

1-methylpiperidin-2-one

Downstream raw materials:

pseudopelletierine

(E)-1',2-dehydro-N-methylpelletierine

Refernces

• 1、 Liebisch,Marekov,Schütte. "Biosynthesis of alkaloids from Punica granatum". . p. 1116 - 1117. Retrieved 1968.
• 2、 Boswell, Henry D.,Draeger, Birgit,Eagles, John,McClintock, Carol,Parr, Adrian,Portsteffen, Andreas,Robins, David J.,Robins, Richard J.,Walton, Nicholas J.,Wong, Chi. "Metabolism of N-alkyldiamines and N-alkylnortropinones by transformed root cultures of Nicotiana and Brugmansia". . p. 855 - 869. Retrieved 2007/10/03.
• 3、 Takahata, Hiroki,Takahashi, Koichi,Wang, Eng-Chi,Yamazaki, Takao. "Alkynylation of Thiolactams. New Synthesis of α-Substituted Pyrrolidine and Piperidine Alkaloids". . p. 1211 - 1214. Retrieved 2007/10/02.