3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine

Base Information

• Chemical Name: 3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine
• CAS No.: 53844-46-5
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• UNII: 3A50Y1J4LP
• DSSTox Substance ID: DTXSID80461155
• Nikkaji Number: J1.826.066B
• Mol file: 53844-46-5.mol

Synonyms:3-(3,4-Dihydro-2H-pyrrol-2-yl)pyridine;isomyosmine;MYMD-1

Chemical Property of 3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 0.00268mmHg at 25°C
• Boiling Point: 295.5oC at 760 mmHg
• Flash Point: 132.5oC
• PSA: 25.25000
• Density: 1.12g/cm3
• LogP: 1.42290
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

90% ^*data from raw suppliers

(+/-)-IsoMyosmine,TechnicalGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N=C1)C2=CN=CC=C2
• Uses: Used in the synthesis of (+/-)-N''-Nitrosonornicotine 5''-Acetate (NNN-5’-OAc), a stable precursor of the active metabolite 5''-hydroxy(+/-)-N''-nitrosonornicotine (NNN-5''-OH). (+/-)-Isomyosmine can be used in the synthesis of (+/-)-N'-Nitrosonornicotine 5'-Acetate (NNN-5’-OAc), a stable precursor of the active metabolite 5'-hydroxy(+/-)-N'-nitrosonornicotine (NNN-5'-OH).

Technology Process of 3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine

There total 7 articles about 3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine 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: 100.0%

(+/-)-N-(3-[1,3]dioxan-2-yl-1-pyridin-3-yl-propyl)-2-methyl-propanesulfinamide → 3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine (53844-46-5)

Guidance literature:

(+/-)-N-(3-[1,3]dioxan-2-yl-1-pyridin-3-yl-propyl)-2-methyl-propanesulfinamide; With water; trifluoroacetic acid; at 20 ℃; for 1h; Inert atmosphere;

With water; sodium hydrogencarbonate;

DOI:10.1021/jo9000417

Reference yield: 26.0%

E-cyclopropyl-(3-pyridinyl)methyleneamine (502546-16-9) → 3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine (53844-46-5)

Guidance literature:

at 350 ℃; under 20 Torr;

DOI:10.1016/S0040-4039(02)02238-4

Reference yield:

3-pyridinecarboxaldehyde (500-22-1) → 3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine (53844-46-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetraethoxy orthosilicate / 18 h / 160 °C

2.1: magnesium; iodine / tetrahydrofuran / 1.25 h / Reflux

2.2: -78 - 20 °C

3.1: iodine; benzol / dichloromethane / 20 °C

4.1: sulfuric acid / 4 h / Heating

With tetraethoxy orthosilicate; benzol; sulfuric acid; iodine; magnesium; In tetrahydrofuran; dichloromethane; 3.1: |Hofmann-Loeffler-Freytag Synthesis;

DOI:10.1021/acs.orglett.8b03909

upstream raw materials:

E-cyclopropyl-(3-pyridinyl)methyleneamine

3-pyridinecarboxaldehyde

Downstream raw materials:

(+/-)-N'-nitrosonornicotine 5'-acetate

3-(1-methyl-pyrrolidin-2-yl)-pyridine

rac-nornicotine

Refernces

• 1、 Marriner, Gwendolyn A.,Kerwin, Sean M.. "An improved synthesis of (±)-N#-nitrosonornicotine 5#-acetate". supporting information; experimental part. p. 2891 - 2892. Retrieved 2009/09/05.
• 2、 Nakane,Hutchinson. "Biosynthetic studies of secondary plant metabolites with 13CO2. Nicotiana alkaloids. 2. New synthesis of nornicotine and nicotine. Quantitative carbon-13 NMR spectroscopic analysis of [2',3',N-CH3-13C3]nicotine". . p. 3922 - 3931. Retrieved 2007/10/04.