5-Hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one

Base Information

• Chemical Name: 5-Hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one
• CAS No.: 184827-12-1
• Molecular Formula: C8H7 N O2
• Molecular Weight: 149.14668
• DSSTox Substance ID: DTXSID601224269
• Nikkaji Number: J1.260.236G
• Mol file: 184827-12-1.mol

Synonyms:184827-12-1;5-hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one;7H-Cyclopenta[c]pyridin-7-one,5,6-dihydro-5-hydroxy-(9CI);SCHEMBL20850458;DTXSID601224269;5,6-Dihydro-5-hydroxy-7H-cyclopenta[c]pyridin-7-one

Chemical Property of 5-Hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one

Chemical Property:

• PSA: 50.19000
• LogP: 0.70140
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

5,6-dihydro-5-hydroxy-7H-Cyclopenta[c]pyridin-7-one 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=C(C1=O)C=NC=C2)O

Technology Process of 5-Hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one

There total 6 articles about 5-Hydroxy-5,6-dihydrocyclopenta[c]pyridin-7-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1-hydroxy-4-methylenocyclopentano[2,3-c]pyridine (184827-10-9,119308-95-1) → 5,6-dihydro-7-hydroxy-5H-[2]pyrindin-7-one (184827-12-1)

Guidance literature:

1-hydroxy-4-methylenocyclopentano[2,3-c]pyridine; With ozone; acetic acid; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2003.09.079

Reference yield:

3-bromo-pyridine-4-carbaldehyde (70201-43-3) → 5,6-dihydro-7-hydroxy-5H-[2]pyrindin-7-one (184827-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / Zn powder / dimethylformamide / 0.5 h / 20 °C

2.1: 80 percent / Ph₃P; Et₃N / Pd(OAc)2 / acetonitrile / 3.5 h / 70 °C

3.1: ozone; AcOH / CH₂Cl₂ / -78 °C

3.2: 85 percent / Me₂S / CH₂Cl₂ / -78 - 20 °C

With ozone; acetic acid; triethylamine; triphenylphosphine; zinc; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Barbier reaction / 2.1: Heck reaction;

DOI:10.1016/j.tet.2003.09.079

Reference yield:

3-bromo-4-(1'-hydroxy-3'-butenyl)pyridine (184827-08-5) → 5,6-dihydro-7-hydroxy-5H-[2]pyrindin-7-one (184827-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / Ph₃P; Et₃N / Pd(OAc)2 / acetonitrile / 3.5 h / 70 °C

2.1: ozone; AcOH / CH₂Cl₂ / -78 °C

2.2: 85 percent / Me₂S / CH₂Cl₂ / -78 - 20 °C

With ozone; acetic acid; triethylamine; triphenylphosphine; palladium diacetate; In dichloromethane; acetonitrile; 1.1: Heck reaction;

DOI:10.1016/j.tet.2003.09.079

upstream raw materials:

1-hydroxy-4-methylenocyclopentano[2,3-c]pyridine

3-bromo-pyridine-4-carbaldehyde

3-bromo-4-(1'-hydroxy-3'-butenyl)pyridine

pyridine-4-carbaldehyde

Downstream raw materials:

1-benzyloxy-4-methylenecyclopentano<2,3-c>pyridine

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