61863-41-0

Usage

Bicyclic amine

has a bicyclo[2.2.1]heptane ring system

Stereochemistry

has two stereocenters

Stereoisomers

three possible stereoisomers

Use in organic synthesis

commonly used as a building block in organic synthesis

Presence in pharmaceutical compounds

can be found in various pharmaceutical compounds

Chemical reactivity

unique chemical reactivity due to its bicyclic structure

Chiral building block

used in the preparation of a variety of chiral drugs and natural products.

InChI:InChI=1/C9H15N/c10-4-3-9-6-7-1-2-8(9)5-7/h1-2,7-9H,3-6,10H2/t7-,8+,9-/m1/s1

Upstream product

• 4003-00-3 2-endo-cyanomethylbicyclo[2.2.1]hept-5-ene 
• 19926-90-0 (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 542-92-7 cyclopenta-1,3-diene 

Relevant academic research and scientific papers

Synthesis and epoxidation of 5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene derivatives

A number of derivatives of 5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene (85-90% of the endo isomer) were synthesized by reactions with p-nitrobenzenesulfonyl chloride, p-toluenesulfonyl chloride, benzoyl chloride, p-nitrobenzoyl chloride, benzyl isocyanate, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride. By reactions of the resulting sulfon- and carboxamides with peroxyphthalic acid generated in situ from phthalic anhydride and 40-45% hydrogen peroxide the corresponding epoxy derivatives were obtained. These reactions were not accompanied by heterocyclization into azabrendane derivatives, which is typical of homologous N-(p-nitrophenylsulfonyl)-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene.

Process for forming perfluorinated-alkyl sulfonamide substituted norbornene-type monomers

Embodiments in accordance with the present invention are directed to providing processes for forming fluorinated-alkyl and particularly perfluorinated-alkyl sulfonamide substituted norbornene-type monomers.

Molecular recognition of DNA by rigid [n]-polynorbornane-derived bifunctional intercalators: Synthesis and evaluation of their binding properties

We have exploited the concept of multivalency in the context of DNA recognition, using novel chemistry to synthesize a new type of bis-intercalator with unusual sequence-selectivity. Bis-intercalation has been observed previously, but design principles for de novo construction of such molecules are not known. Our compounds feature two aromatic moieties projecting from a rigid, polynorbornane-based scaffold. The length and character of the backbone as well as the identity of the intercalators were varied, resulting in mono- or divalent recognition of the double helix with varying affinity. Our lead compound proved to be a moderately sequence-selective bis-intercalator with an unwinding angle of 27° and a binding constant of about 8 μM. 9-Aminoacridine rings were preferred over acridine carboxamides or naphthalimides, and a rigid [3]-polynorbornane scaffold was superior to a [5]-polynorbornane. The flexibility of the linker connecting the rings to the scaffold, although less influential, could affect the strength and character of the DNA binding.