45347-36-2

Usage

Cyclopropane-containing Diamine

It contains a cyclopropane ring and two amine groups (-NH2).

Chiral Center

The presence of a chiral center allows the molecule to exist in two enantiomeric forms.

Enantiomeric Forms

The compound has two non-superimposable mirror images, which are called enantiomers.

(1R,2S)-relConfiguration

This notation describes the specific spatial arrangement of atoms in the molecule, which is crucial for its chemical and biological properties.

Organic Synthesis

1,2-Cyclopropanediamine, (1R,2S)-relis used as a chiral building block in the synthesis of various organic compounds.

Pharmaceutical and Agrochemical Production

The compound is utilized in the production of pharmaceuticals and agrochemicals due to its chiral nature and unique structural features.

Asymmetric Catalysis

It has been studied for its potential application in asymmetric catalysis, a process that involves the selective transformation of prochiral molecules into enantiomerically enriched products.

Chemical and Biological Properties

The (1R,2S)-relconfiguration of the molecule plays a significant role in determining its chemical reactivity and interactions with biological systems.

Upstream product

• 100-52-7 benzaldehyde 
• 79082-67-0 trans-1,2-cyclopropanediammonium dibromide 

Downstream Products

• 65424-87-5 cis-2,3-Bis(2,4,6-trimethylphenyl)-2,3-dihydro-1H-1,4-diazepin 
• 731-65-7 cis-2,3-Dihydro-2,3-diphenyl-1H-1,4-diazepine 
• 65424-88-6 cis-2,3-Bis(2-hydroxyphenyl)-2,3-dihydro-1H-1,4-diazepin 
• 65424-86-4 cis-2,3-Bis(4-methylphenyl)-2,3-dihydro-1H-1,4-diazepin 

Relevant academic research and scientific papers

Pyrroles from 1,2-cyclopropanediamines and aldehydes

Mechanistic investigations by means of proton spectroscopy detected intermediates and uncovered the course of reactions in acetate-buffered [D4]methanol of primary cyclopropanediamines cis- and trans-2a with benzaldehyde (3a) or 2,2-dimethylpropanal (3b), of secondary cyclopropanediamines cis- and trans-2b with 3b, and of the ringmethylated cyclopropanediamine trans-14a and the aromatic aldehydes 3a and c. This study provided the basis of an expedient synthesis of pyrroles which takes place under exceptionally mild conditions. Irrespective of the configuration, primary (2a·2HBr) and secondary cyclopropanediammonium dibromides 2b and c·2HBr that are devoid of ring substituents react with aromatic aldehydes 3a, e-h, cinnamic aldehyde (3i), and 3b to afford 2-substituted (8a, b) and 1,2-disubstituted pyrroles (8c-i), respectively. The 3-substituted secondary transcyclopropanediammonium dibromides 24·2HBr furnish 1,2,4-trisubstituted pyrroles 25. While the primary 1-methylcyclopropanediammonium dibromide trans-14a·2HBr reacts regioselectively with 3a and c to produce only 2,3-substituted pyrroles 19a, c, the corresponding secondary dibromide trans-14c·2HBr gives rise to the formation of mixtures of 1,2,3- (22) and 1,2,5-trisubstituted pyrroles 23. The key step of pyrrole formation from 1,2-cyclopropanediamines and aldehydes is the ring expansion of intermediate monoiminium ions of type 5 via azomethine ylides (E,Z)-6 to yield dihydropyrrolium ions 7.