150851-98-2

Basic information

• Product Name: (1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene
• Synonyms: 2-Azabicyclo[2.2.1]hept-5-ene, 2-(phenylmethyl)-, (1R,4S)-
• CAS NO: 150851-98-2
• Molecular Formula: C13H15N
• Molecular Weight: 185.2649
• Mol File: 150851-98-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene(150851-98-2)
• EPA Substance Registry System: (1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene(150851-98-2)

Safety Data

• Hazardous Substances Data: 150851-98-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity make it a versatile building block for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
(1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene is used as a starting material or a synthetic intermediate in the development of new pharmaceuticals. Its unique stereochemistry and functional groups can be exploited to design and synthesize novel drug candidates with potential therapeutic applications.
Used in Pharmaceutical Industry:
(1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene is used as an active pharmaceutical ingredient (API) or as a key component in the synthesis of APIs. Its unique properties and reactivity make it a promising candidate for the development of new drugs with improved efficacy, selectivity, and safety profiles.
Used in Research and Development:
(1S,4R)-5-benzyl-5-azabicyclo[2.2.1]hept-2-ene is used as a research tool in academic and industrial laboratories to study the structure-activity relationships of various biologically active compounds. Its unique stereochemistry and reactivity can provide valuable insights into the design and optimization of new drug candidates and other chemical entities.

Upstream product

• 50-00-0 formaldehyd 
• 3287-99-8 benzylamine hydrochloride 
• 542-92-7 cyclopenta-1,3-diene 
• 100-39-0 benzyl bromide 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 100-46-9 benzylamine 

Downstream Products

• 745836-21-9 anti-2-azabicyclo[2.2.1]heptane-7-carboxylic acid ethyl ester 

Relevant articles and documents

RuO4-catalyzed oxidation reactions of isoxazolino-2- azanorbornane derivatives: A short-cut synthesis of tricyclic lactams and peptidomimetic γ-amino acids

A rapid access to peptidomimetic conformationally constrained γ-amino acids has been developed through the efficient RuO4-mediated oxidation of regioisomeric isoxazolino-2-azanorbornane derivatives. The key intermediates are tricyclic lactams,

Structure-reactivity relationships of zwitterionic 1,3-diaza-Claisen rearrangements

Bridged bicyclic tertiary allylic amines aza-norbornene 1 and isoquinuclidene 2 add to isocyanates, isothiocyanates, and in situ-generated carbodiimides to form zwitterionic intermediates that undergo 1,3-diaza-Claisen rearrangements to afford highly substituted ureas, thioureas, and guanidines, respectively. Aza-norbornene 1 is significantly more reactive toward 1,3-diaza-Claisen rearrangements than isoquinuclidene 2. This reactivity difference is most likely due to the inherent ring strain in the aza-bicyclo[2.2.1]heptene ring system of aza-norbornene 1. The most apparent reactivity trend of the heterocumulenes is that the most electron-deficient heterocumulenes are more reactive toward 1,3-diaza-Claisen rearrangements. The introduction of a new stereocenter α- to the nucleophilic nitrogen in aza-norbornene 1 and isoquinuclidine 2 decreases the reactivity toward 1,3-diaza-Claisen rearrangements, while the exodiastereomers 3b and 4b are less reactive than the corresponding endodiastereomers 3a and 4a. Isocyanates that bear an electron-withdrawing group react with allylic amines 1-3b to afford mixtures of ureas and isoureas; however, with excess isocyanate and heat, thermodynamic equilibration is possible affording ureas. Inspired by this observation, a one-pot reaction of isocyanates with amines 1, 2, and 3b followed by BF3·OEt2-catalyzed isomerization of the urea/isourea mixture was developed that affords the corresponding ureas in excellent yields.

Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions

A novel approach to useful aminols for the synthesis of carbocyclic nucleosides is reported starting from a convenient source, the 2-azanorborn-5-enes. These are readily available through the Grieco cycloaddition of cyclopentadiene with iminium salts and

Rearrangement of 2-azanorbornenes to tetrahydrocyclopenta[c]pyridines under the action of activated alkynes – A short pathway for construction of the altemicidin core

A simple approach to a series of 2,4a,7,7a-tetrahydro-1H-cyclopenta[c]pyridines was proposed on the basis of the amino-Claisen rearrangement of readily accessible 2-azabicyclo[2.2.1]hept-5-enes under the action of dialkyl acetylenedicarboxylates, methyl propiolate or propiolamide. The rearrangement is highly diastereoselective and leads to the formation of only one isomer with cis-annulation of the five- and six-membered rings in satisfactory yields. Using the developed method, close analogs of the altemicidin and SB-203207 cores were synthesized.

SUBSTITUTED 2-AZABICYCLES AND THEIR USE AS OREXIN RECEPTOR MODULATORS

The present invention is directed to compounds of Formula I: wherein X is N or CR1; Y is N or CR2; R1 is H, alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxazole, oxadiazolyl, or pyrazolyl; R2 is H, alkyl, alkoxy, or halo; Z is NH or O; R3 is H, alkyl, alkoxy, halo, or triazolyl; R4 is H or alkyl; or R3 and R4, together with the atoms to which they are attached, form a 6-membered aryl ring or a 5- or 6-membered heteroaryl ring; R5 is pyridyl, pyrazinyl, or pyrimidinyl, wherein the pyridyl, pyrazinyl, or pyrimidinyl is optionally substituted with halo or alkyl; and n is 1 or 2. Methods of making the compounds of Formula I are also described. The invention also relates to pharmaceutical compositions comprising compounds of Formula I. Methods of using the compounds of the invention are also within the scope of the invention.

Polysulfones of new structural types as perspective antioxidant agents

A series of polysulfones of new structural types on the basis of azanorbornenes, 2,2-diallyl-1,1,3,3-tetraethylguanidiniumchloride and tris(diethylamino)diallylaminophosphonium salts were obtained by free radical polymerization reaction. Their antioxidant

From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions

A rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed through the Grieco cycloaddition of cyclopentadiene to iminium salts. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target amin

Chlorination/cyclodehydration of amino alcohols with SOCl2: An old reaction revisited

(Chemical Equation Presented) A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl2 has been developed. This approach obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.

A 1,3-Diaza-Claisen rearrangement that affords guanidines

(Chemical Equation Presented) N-Alkyl-N′-tosylthioureas activated by EDCI react with azanorbonenes at room temperature through a 1,3-diaza-Claisen rearrangement, affording highly substituted, bicyclic guanidines in moderate to good yields.

7-oxo-2-azabicyclo[2.2.1]heptanes as selective muscarinic receptor antagonist

The present invention relates to muscarinic receptor modulators, specifically, 7-oxo-2-azabicyclo[2.2.1]heptanes of formula (I) which are useful for the treatment of various diseases and conditions, for example, Alzheimer's disease, glaucoma, psychosis, particularly schizophrenia or schizophreniform conditions, mania, pain, bipolar disorder, depression, sleeping disorders, epilepsy, gastrointestinal motility disorders, urinary incontinence, and cognition enhancement.