(4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde

Base Information

• Chemical Name: (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde
• CAS No.: 1334496-46-6
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354

Synonyms:(4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde

Chemical Property of (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde

There total 3 articles about (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde 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: 50.0%

2-((1S,2R,3S)-5-methyl-2-nitro-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)acetaldehyde (1334496-18-2) + acrolein (107-02-8,25068-14-8) → (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde (1334496-46-6)

Guidance literature:

With tetramethylguanidine; In dichloromethane; at 20 ℃; for 60h;

DOI:10.1002/anie.201102013

Reference yield:

5-methyl-hexadien-trans-2,4-al (17424-21-4) → (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde (1334496-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid / 1,4-dioxane / 96 h / 55 °C

2: tetramethylguanidine / dichloromethane / 60 h / 20 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid; In 1,4-dioxane; dichloromethane; 1: Diels-Alder reaction;

DOI:10.1002/anie.201102013

Reference yield:

(2-nitroethenyl)benzene (102-96-5) → (4aS,8S,8aR)-6-methyl-8a-nitro-8-phenyl-1,4,4a,7,8,8a-hexahydronaphthalene-2-carbaldehyde (1334496-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid / 1,4-dioxane / 96 h / 55 °C

2: tetramethylguanidine / dichloromethane / 60 h / 20 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid; In 1,4-dioxane; dichloromethane; 1: Diels-Alder reaction;

DOI:10.1002/anie.201102013

upstream raw materials:

2-((1S,2R,3S)-5-methyl-2-nitro-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)acetaldehyde

acrolein

5-methyl-hexadien-trans-2,4-al

(2-nitroethenyl)benzene

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