(2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one

Base Information

• Chemical Name: (2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one
• CAS No.: 74133-16-7
• Molecular Formula: C16H25N3O2
• Molecular Weight: 291.3886
• Mol file: 74133-16-7.mol

Synonyms:

Chemical Property of (2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one

Chemical Property:

• Vapor Pressure: 2.18E-12mmHg at 25°C
• Boiling Point: 537.6°C at 760 mmHg
• Flash Point: 278.9°C
• Density: 1.073g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one

There total 8 articles about (2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-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: 68.0%

(-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one (166373-40-6) → (-)-(2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one (74133-16-7)

Guidance literature:

With (+/-)-trans-2-(butylsulfonyl)-3-phenyloxaziridine; In dichloromethane; for 0.666667h;

DOI:10.1002/hlca.19960790417

Reference yield:

3-Amino-3-phenylpropionic acid (3646-50-2) → (-)-(2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one (74133-16-7)

Guidance literature:

Multi-step reaction with 7 steps

1: HCl gas / 1 h / Heating

2: 93 percent / 3 h / 125 - 135 °C

3: 31 percent / NaBH₃CN / acetic acid / 1 h / 50 °C / before heating 2 h, after heating 23 h room temperature

4: 83 percent / NaOEt / toluene / 5 h

5: 87 percent / hydrogen / Raney Ni / aq. NH₃; aq. ethanol / 14 h / 2585.7 Torr

6: 88 percent / NaOH / aq. ethanol / 264 h / 55 °C

7: 68 percent / (+/-)-trans-2-(butylsulfonyl)-3-phenyloxaziridine / CH₂Cl₂ / 0.67 h

With hydrogenchloride; sodium hydroxide; (+/-)-trans-2-(butylsulfonyl)-3-phenyloxaziridine; hydrogen; sodium ethanolate; sodium cyanoborohydride; nickel; In ammonium hydroxide; ethanol; dichloromethane; acetic acid; toluene;

DOI:10.1002/hlca.19960790417

Reference yield:

(3S)-methyl 3-amino-3-phenylpropanoate (37088-66-7) → (-)-(2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-one (74133-16-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / 3 h / 125 - 135 °C

2: 31 percent / NaBH₃CN / acetic acid / 1 h / 50 °C / before heating 2 h, after heating 23 h room temperature

3: 83 percent / NaOEt / toluene / 5 h

4: 87 percent / hydrogen / Raney Ni / aq. NH₃; aq. ethanol / 14 h / 2585.7 Torr

5: 88 percent / NaOH / aq. ethanol / 264 h / 55 °C

6: 68 percent / (+/-)-trans-2-(butylsulfonyl)-3-phenyloxaziridine / CH₂Cl₂ / 0.67 h

With sodium hydroxide; (+/-)-trans-2-(butylsulfonyl)-3-phenyloxaziridine; hydrogen; sodium ethanolate; sodium cyanoborohydride; nickel; In ammonium hydroxide; ethanol; dichloromethane; acetic acid; toluene;

DOI:10.1002/hlca.19960790417

upstream raw materials:

(-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one

3-Amino-3-phenylpropionic acid

(3S)-methyl 3-amino-3-phenylpropanoate

(S)-4-phenyl-1,5-diazacyclononan-2-one

Downstream raw materials:

(-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one

Refernces

Decomposition of N-hydroxylated compounds during atmospheric pressure chemical ionization

10.1002/jms.1703

The research discusses the decomposition of N-hydroxylated compounds during atmospheric pressure chemical ionization (APCI) in liquid chromatography-mass spectrometry (LC-APCI-MS) experiments. The study aimed to understand and control artifact formation from N-hydroxylamines by APCI, which is crucial for accurate mass spectrometry analysis, particularly in the study of natural products and drug metabolism. The researchers used a synthetic N-hydroxylated tetraamine derivative as a model compound to investigate the reduction, oxidation, and water elimination reactions that occur during APCI, leading to the generation of amines, N-oxides, and imines. They found that the decomposition depends on the analyte concentration and the acidity of the solution, and they developed an MS method to unambiguously identify N–OH functionalities. The method was applied to study natural products, including polyamine toxins from spider venom and mayfoline, a cyclic polyamine derivative. The chemicals used in the process included high-performance liquid chromatography (HPLC) grade solvents such as acetonitrile, trifluoroacetic acid, formic acid, and aqueous ammonia solution, as well as synthetic compounds like [4-hydroxy-9-(2-nitrobenzenesulfonyl)-4,9-diazadodecane]1,12-diphthalimide and mayfoline. The study concluded that understanding in-source decomposition of N-hydroxylated amines can prevent misinterpretation of MS data and help distinguish N- from C-hydroxylation in compounds.