1-Pyrrolidino-1-cyclohexene

Base Information

• Chemical Name: 1-Pyrrolidino-1-cyclohexene
• CAS No.: 1125-99-1
• Molecular Formula: C10H17 N
• Molecular Weight: 151.252
• Hs Code.: 29339980
• European Community (EC) Number: 214-414-6
• NSC Number: 29652
• DSSTox Substance ID: DTXSID00150079
• Nikkaji Number: J80.185B
• Wikidata: Q72505231
• Mol file: 1125-99-1.mol

Synonyms:1-pyrrolidino-1-cyclohexene

Chemical Property of 1-Pyrrolidino-1-cyclohexene

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 0.0571mmHg at 25°C
• Melting Point: 113 °C
• Refractive Index: n20/D 1.5217(lit.)
• Boiling Point: 114-115 ºC (15 mmHg)
• PKA: 8.91±0.20(Predicted)
• Flash Point: 39 ºC
• PSA: 3.24000
• Density: 0.94
• LogP: 2.47800
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 151.136099547
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

97% ^*data from raw suppliers

1-Pyrrolidino-1-cyclohexene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-20/21/22
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=CC1)N2CCCC2

Technology Process of 1-Pyrrolidino-1-cyclohexene

There total 9 articles about 1-Pyrrolidino-1-cyclohexene 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%

pyrrolidine (123-75-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1)

Guidance literature:

In toluene; for 18h; Molecular sieve; Dean-Stark trap; Heating / reflux;

Reference yield: 80.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 12h; Heating;

DOI:10.1002/hlca.200790050

Reference yield:

pyrrolidine (123-75-1) + 1-bromocyclohex-1-ene (2044-08-8) → 1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate; In toluene; at 80 ℃;

DOI:10.1039/b508464d

upstream raw materials:

pyrrolidine

cyclohexanone

1-Pyrrolidin-1-yl-cyclohexanecarbonitrile

1-bromocyclohex-1-ene

Downstream raw materials:

2-(Pyrrolidin-1-yl)bicyclo[3.3.1]nonan-9-on

ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

2-(2-[2]naphthyl-ethyl)-cyclohexanone

ethyl 2-oxocyclohexane carboxylate

Refernces

Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives

10.1016/j.tetlet.2003.11.133

The study presents a concise synthesis method for a novel class of homochiral aromatic amino acid surrogates, featuring tetrahydroindazole or benzisoxazole systems. These surrogates were synthesized through the acylation of cyclic 1,3-diketone by the side-chain carboxyl functionality of specific amino acid precursors, followed by a regioselective condensation with hydrazine, N-benzylhydrazine, and hydroxylamine. The synthetic strategy is versatile, allowing for the creation of structurally diverse derivatives. These novel amino acids can be efficiently incorporated into proteins and have potential applications in imparting unique properties to biological peptides. The study also includes the synthesis of Na-Fmoc-protected derivatives, which are useful for solid-phase peptide assembly, and the exploration of the stereochemistry integrity of the homochiral starting material through chemical transformations. The synthesized amino acids offer opportunities as structural surrogates of tryptophan and as building blocks for designing molecular probes.