(1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone

Base Information

• Chemical Name: (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone
• CAS No.: 849664-69-3
• Molecular Formula: C₁₈H₁₈N₂O₄S
• Molecular Weight: 358.418

Synonyms:(1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone

Chemical Property of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone

There total 5 articles about (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-methanone 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: 62.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 1-((3aS,6aS)-4,4-Dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-propenone (849664-45-5) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-methanone (849664-69-3) + (1S,2S,4S)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-methanone

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tetasy.2004.12.026

Reference yield:

benzonitrile oxide (873-67-6) → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-methanone (849664-69-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chlorosuccinimide; pyridine / CH₂Cl₂ / 0.83 h / 20 - 40 °C

1.2: 82 percent / triethylamine / CH₂Cl₂; toluene / 24 h / 20 °C

2.1: tetrahydrofuran / 24 h / Heating

2.2: phosphorus oxychloride / tetrahydrofuran / 12 h / Heating

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

3.1: formic acid / 8 h / 70 °C

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

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

4.2: 37 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 62 percent / titanium(IV) chloride / CH₂Cl₂ / -78 - 20 °C

With pyridine; N-chloro-succinimide; n-butyllithium; formic acid; titanium tetrachloride; In tetrahydrofuran; hexane; dichloromethane; 5.1: Diels-Alder reaction;

DOI:10.1016/j.tetasy.2004.12.026

Reference yield:

(3aR,6aR)-3-Phenyl-6,6a-dihydro-3aH-1,5-dioxa-4-thia-2-aza-pentalene 4,4-dioxide → (1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-((3aS,6aS)-4,4-dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ6-thia-2,5-diaza-pentalen-5-yl)-methanone (849664-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 24 h / Heating

1.2: phosphorus oxychloride / tetrahydrofuran / 12 h / Heating

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

2.1: formic acid / 8 h / 70 °C

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

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

3.2: 37 percent / tetrahydrofuran; hexane / -78 - 20 °C

4.1: 62 percent / titanium(IV) chloride / CH₂Cl₂ / -78 - 20 °C

With n-butyllithium; formic acid; titanium tetrachloride; In tetrahydrofuran; hexane; dichloromethane; 4.1: Diels-Alder reaction;

DOI:10.1016/j.tetasy.2004.12.026

upstream raw materials:

cyclopenta-1,3-diene

1-((3aS,6aS)-4,4-Dioxo-3-phenyl-3a,4,6,6a-tetrahydro-1-oxa-4λ⁶-thia-2,5-diaza-pentalen-5-yl)-propenone

benzonitrile oxide

(3aS,6aS)-3-Phenyl-5-((S)-1-phenyl-ethyl)-3a,5,6,6a-tetrahydro-1-oxa-4-thia-2,5-diaza-pentalene 4,4-dioxide

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