Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-

Base Information

• Chemical Name: Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-
• CAS No.: 871468-89-2
• Molecular Formula: C14H16O2
• Molecular Weight: 216.28
• DSSTox Substance ID: DTXSID60470725
• Nikkaji Number: J2.258.535E
• Wikidata: Q82298887
• Mol file: 871468-89-2.mol

Synonyms:871468-89-2;Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-;DTXSID60470725

Chemical Property of Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 216.115029749
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)C=O)CC(=O)C2=CC=CC=C2
• Isomeric SMILES: C1C[C@H]([C@H](C1)C=O)CC(=O)C2=CC=CC=C2

Technology Process of Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-

There total 9 articles about Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)- 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:

(E)-8-hydroxy-1-phenyloct-2-en-1-one (871468-88-1) → (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde (871468-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / TEMPO; KBr; aq. NaOCl / NaHCO₃ / CH₂Cl₂ / 0.5 h / -10 °C

2: (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide*CF₃COOH / acetone / 4 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide trifluoroacetate; potassium bromide; sodium hydrogencarbonate; In dichloromethane; acetone; 2: Michael reaction;

DOI:10.1021/ja055740s

Reference yield:

1-phenyl-8-(tetrahydropyran-2-yloxy)-oct-2-en-1-one (871468-87-0) → (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde (871468-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / aq. TsOH / tetrahydrofuran / 12 h / 50 °C

2: 73 percent / TEMPO; KBr; aq. NaOCl / NaHCO₃ / CH₂Cl₂ / 0.5 h / -10 °C

3: (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide*CF₃COOH / acetone / 4 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide trifluoroacetate; toluene-4-sulfonic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetone; 3: Michael reaction;

DOI:10.1021/ja055740s

Reference yield:

3-hydroxy-1-phenyl-8-(tetrahydropyran-2-yloxy)-octan-1-one (871468-86-9) → (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde (871468-89-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Ac₂O; pyridine; DMAP / 48 h / 50 °C

2: 88 percent / aq. TsOH / tetrahydrofuran / 12 h / 50 °C

3: 73 percent / TEMPO; KBr; aq. NaOCl / NaHCO₃ / CH₂Cl₂ / 0.5 h / -10 °C

4: (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide*CF₃COOH / acetone / 4 h / 0 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide trifluoroacetate; acetic anhydride; toluene-4-sulfonic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetone; 4: Michael reaction;

DOI:10.1021/ja055740s

upstream raw materials:

E-8-phenyl-8-oxo-6-octenal

(E)-8-hydroxy-1-phenyloct-2-en-1-one

1-phenyl-8-(tetrahydropyran-2-yloxy)-oct-2-en-1-one

3-hydroxy-1-phenyl-8-(tetrahydropyran-2-yloxy)-octan-1-one

Downstream raw materials:

(1R,2S)-(-)-2-(2-oxo-2-phenylethyl)cyclopentanecarboxylic acid methyl ester

(1R,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde

Refernces

• 1、 Yang, Jung Woon,Hechavarria Fonseca, Maria T.,List, Benjamin. "Catalytic asymmetric reductive Michael cyclization". . p. 15036 - 15037. Retrieved 2007/10/03.