184827-13-2

Basic information

• Product Name: 5H-Cyclopenta[c]pyridine, 6,7-dihydro-7-methylene-5-(phenylmethoxy)-
• CAS NO: 184827-13-2
• Molecular Formula: C16H15NO
• Molecular Weight: 237.301
• Mol File: 184827-13-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5H-Cyclopenta[c]pyridine, 6,7-dihydro-7-methylene-5-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Cyclopenta[c]pyridine, 6,7-dihydro-7-methylene-5-(phenylmethoxy)-(184827-13-2)
• EPA Substance Registry System: 5H-Cyclopenta[c]pyridine, 6,7-dihydro-7-methylene-5-(phenylmethoxy)-(184827-13-2)

Safety Data

• Hazardous Substances Data: 184827-13-2(Hazardous Substances Data)

Upstream product

• 160540-49-8 4-(1-benzyloxy-2-bromo)-3-ethynylpyridine 
• 100-39-0 benzyl bromide 
• 184827-12-1 5,6-dihydro-7-hydroxy-5H-[2]pyrindin-7-one 
• 160540-47-6 4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine 
• 160540-48-7 4-(1-benzyloxy-2-hydroxy)-3-ethynylpyridine 
• 160540-44-3 3-bromo-4-(2-tetrahydropyranyloxyacetyl)pyridine 
• 626-55-1 3-Bromopyridine 
• 184827-10-9 1-hydroxy-4-methylenocyclopentano[2,3-c]pyridine 
• 184827-09-6 3-bromo-4-(but-3-yn-1-ol)pyridine 
• 70201-43-3 3-bromo-pyridine-4-carbaldehyde 
• 872-85-5 pyridine-4-carbaldehyde 

Downstream Products

• 160540-51-2 1-benzyloxy-4-oxocyclopentano<2,3-c>pyridine 

Relevant articles and documents

Pyridine radicals in synthesis. Part 3: Cyclopentannulation of pyridine via the 3-pyridyl radical and a formal synthesis of (±)-oxerine

The allylation and propargylation of 3-bromo-4-formylpyridine under zinc-mediated Barbier conditions is described. The homoallylic alcohols produced are cyclised via the derived 3-pyridyl radical to give cyclopentannulated pyridines. One of these bicyclic compounds is converted into an advanced intermediate in a previous synthesis of the monoterpene alkaloid (±)-oxerine. (C) 2000 Elsevier Science Ltd.

First Total Synthesis of (+/-)-Oxerine

Total synthesis of (+/)-oxerine (1), a monoterpene alkaloid, starting from 3-bromopyridine (7) is described.The key reaction in this sequence is the samarium iodide (SmI2)-mediated intramolecular cyclization of γ-ethynyl bromide (4).