1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone

Base Information

• Chemical Name: 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone
• CAS No.: 849664-58-0
• Molecular Formula: C₂₀H₂₀N₂O₄S
• Molecular Weight: 384.456

Synonyms:1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone

Chemical Property of 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone

Chemical Property:

Purity/Quality:

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Technology Process of 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone

There total 4 articles about 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone 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: 33.0%

acryloyl chloride (814-68-6,25189-84-8) + (3R,3aR,6aR)-2-Benzyl-3-phenyl-hexahydro-1-oxa-4-thia-2,5-diaza-pentalene 4,4-dioxide (849664-29-5) → 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-propenone (849664-58-0)

Guidance literature:

(3R,3aR,6aR)-2-Benzyl-3-phenyl-hexahydro-1-oxa-4-thia-2,5-diaza-pentalene 4,4-dioxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

acryloyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1016/j.tetasy.2004.12.026

Reference yield:

N-Benzylidenebenzylamine N-oxide (3376-26-9) → 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-propenone (849664-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / toluene / 24 h / 120 °C

2.1: tetrahydrofuran / 24 h / Heating

2.2: phosphorus oxychloride / tetrahydrofuran / 12 h / Heating

2.3: 43 percent / 4-(dimethylamino)pyridine; triethylamine / tetrahydrofuran / 36 h / Heating

3.1: formic acid / 8 h / 70 °C

3.2: 40 percent / potassium hydroxide / ethanol / 12 h / 20 °C

4.1: n-butyl lithium / tetrahydrofuran; hexane / -78 - 20 °C

4.2: 33 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; formic acid; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/j.tetasy.2004.12.026

Reference yield:

(3S,3aS,6aS)-2-Benzyl-3-phenyl-tetrahydro-1,5-dioxa-4-thia-2-aza-pentalene 4,4-dioxide → 1-((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-propenone (849664-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 24 h / Heating

1.2: phosphorus oxychloride / tetrahydrofuran / 12 h / Heating

1.3: 43 percent / 4-(dimethylamino)pyridine; triethylamine / tetrahydrofuran / 36 h / Heating

2.1: formic acid / 8 h / 70 °C

2.2: 40 percent / potassium hydroxide / ethanol / 12 h / 20 °C

3.1: n-butyl lithium / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 33 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; formic acid; In tetrahydrofuran; hexane;

DOI:10.1016/j.tetasy.2004.12.026

upstream raw materials:

acryloyl chloride

(3R,3aR,6aR)-2-Benzyl-3-phenyl-hexahydro-1-oxa-4-thia-2,5-diaza-pentalene 4,4-dioxide

N-Benzylidenebenzylamine N-oxide

(3R,3aR,6aR)-2-Benzyl-3-phenyl-5-((S)-1-phenyl-ethyl)-hexahydro-1-oxa-4-thia-2,5-diaza-pentalene 4,4-dioxide

Downstream raw materials:

((3R,3aR,6aR)-2-Benzyl-4,4-dioxo-3-phenyl-hexahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl-methanone

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