205442-89-3

Basic information

• Product Name: (3S,5R,7AR)-5-(BENZOTRIAZOL-1-YL)-3-PHENYL[2,1-B]OXAZOLOPYRROLIDINE
• Synonyms: 1H-Benzotriazole,1-(hexahydro-3-phenylpyrrolo[2,1-b]oxazol-5-yl)-, [3S-(3a,5a,7aa)]-
• CAS NO: 205442-89-3
• Molecular Formula: C₁₈H₁₈N₄O
• Molecular Weight: 306.367
• Mol File: 205442-89-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,5R,7AR)-5-(BENZOTRIAZOL-1-YL)-3-PHENYL[2,1-B]OXAZOLOPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R,7AR)-5-(BENZOTRIAZOL-1-YL)-3-PHENYL[2,1-B]OXAZOLOPYRROLIDINE(205442-89-3)
• EPA Substance Registry System: (3S,5R,7AR)-5-(BENZOTRIAZOL-1-YL)-3-PHENYL[2,1-B]OXAZOLOPYRROLIDINE(205442-89-3)

Safety Data

• Hazardous Substances Data: 205442-89-3(Hazardous Substances Data)

Usage

General Description

(3S,5R,7AR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine is a chemical compound with a complex molecular structure. It contains a benzotriazol-1-yl group, a phenyl group, and an oxazolopyrrolidine ring. (3S,5R,7AR)-5-(BENZOTRIAZOL-1-YL)-3-PHENYL[2,1-B]OXAZOLOPYRROLIDINE may have potential pharmaceutical applications due to its unique structure and potential biological activity. The presence of the benzotriazol-1-yl and phenyl groups suggests that it may have UV-absorbing properties, making it potentially useful in sunscreen and sunblock formulations. Additionally, the oxazolopyrrolidine ring may make it useful in the development of drugs targeting specific biological pathways. Further research and testing are needed to fully understand the potential uses and properties of this compound.

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 638-37-9 butanedial 
• 20989-17-7 (2S)-2-phenylglycinol 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 2592-95-2 benzotriazol-1-ol 
• 2935-35-5 (S)-2-phenylglycine 

Downstream Products

• 205442-90-6 (3S,5S,7aR)-3,5-diphenylhexahydropyrrolo<2,1-b><1,3>oxazole 
• 205442-98-4 (S)-2-((2R,5R)-2,5-Dipropyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205442-93-9 (S)-2-((2S,5R)-2,5-Dipropyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205442-99-5 (S)-2-((2R,5R)-2,5-Dipentyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205442-94-0 (S)-2-((2S,5R)-2,5-Dipentyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205443-00-1 (S)-2-((2R,5R)-2,5-Diphenethyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205442-95-1 (S)-2-((2R,5S)-2,5-Diphenethyl-pyrrolidin-1-yl)-2-phenyl-ethanol 
• 205442-92-8 (2S)-2-(2R,5S)-2,5-dimethyltetrahydro-1H-1-pyrrolyl-2-phenylethan-1-ol 
• 1187481-40-8 (2S)-2-[(2R,5S)-2,5-dibenzyltetrahydro-1H-pyrrol-1-yl]-2-phenylethanol 
• 1436696-58-0 C₃₀H₃₃NO₅ 
• 1436696-32-0 C₃₀H₃₃NO₅ 
• 1436696-61-5 C₃₂H₄₁NO₅ 
• 1436696-35-3 C₃₂H₄₁NO₅ 
• 1436696-64-8 C₂₈H₂₉F₄NO 

Relevant articles and documents

Pyrrolidine analogs of GZ-793A: Synthesis and evaluation as inhibitors of the vesicular monoamine transporter-2 (VMAT2)

Central heterocyclic ring size reduction from piperidinyl to pyrrolidinyl in the vesicular monoamine transporter-2 (VMAT2) inhibitor GZ-793A and its analogs resulted in novel N-propane-1,2(R)-diol analogs 11a-i. These compounds were evaluated for their affinity for the dihydrotetrabenazine (DTBZ) binding site on VMAT2 and for their ability to inhibit vesicular dopamine (DA) uptake. The 4-difluoromethoxyphenethyl analog 11f was the most potent inhibitor of [3H]-DTBZ binding (Ki = 560 nM), with 15-fold greater affinity for this site than GZ-793A (Ki = 8.29 μM). Analog 11f also showed similar potency of inhibition of [3H]-DA uptake into vesicles (Ki = 45 nM) compared to that for GZ-793A (Ki = 29 nM). Thus, 11f represents a new water-soluble inhibitor of VMAT function.

Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine

Benzotriazole, 2,5-dimethoxytetrahydrofuran, and (S)-phenylglycinol in one step gave 80% of (3S, 5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl-[2,1- b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5- disubstituted pyrrolidines.