(4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone

Base Information

• Chemical Name: (4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone
• CAS No.: 112740-65-5
• Molecular Formula: C₂₁H₁₆O₄S
• Molecular Weight: 364.422

Synonyms:(4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone

Chemical Property of (4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone

Chemical Property:

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Technology Process of (4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone

There total 6 articles about (4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone 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: 90.0%

(1R*,4aR*,9aR*)-5-methoxy-9a-(phenylthio)-1-<(trimethylsilyl)oxy>-1,4,4a,9a-tetrahydro-9,10-anthraquinone (112740-64-4) → (4aR*,9aR*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone (112740-65-5)

Guidance literature:

With jones reagent; In acetone; at 0 ℃;

DOI:10.1021/jo00242a042

Reference yield:

5-acetoxy-2-bromo-1,4-naphthoquinone (77189-69-6) → (4aR*,9aR*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone (112740-65-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / KOH / methanol; tetrahydrofuran / 2.5 h / Ambient temperature

2: 100 percent / 12 N aq. HCl / ethanol / 0.25 h / Heating

3: 91 percent / Ag₂O / CH₂Cl₂ / 15 h

4: 79 percent / CH₂Cl₂ / 78 h / Heating

5: 90 percent / Jones reagent / acetone / 0 °C

With hydrogenchloride; potassium hydroxide; jones reagent; silver(l) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone;

DOI:10.1021/jo00242a042

Reference yield:

5-methoxy-2-(phenylthio)-1,4-naphthoquinone (105259-49-2) → (4aR*,9aR*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone (112740-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CH₂Cl₂ / 78 h / Heating

2: 90 percent / Jones reagent / acetone / 0 °C

With jones reagent; In dichloromethane; acetone;

DOI:10.1021/jo00242a042

upstream raw materials:

(1R^*,4aR^*,9aR^*)-5-methoxy-9a-(phenylthio)-1-<(trimethylsilyl)oxy>-1,4,4a,9a-tetrahydro-9,10-anthraquinone

5-acetoxy-2-bromo-1,4-naphthoquinone

5-methoxy-2-(phenylthio)-1,4-naphthoquinone

5-acetoxy-2-(phenylthio)-1,4-naphthoquinone

Downstream raw materials:

1,5-dimethoxy-anthraquinone

1-hydroxy-5-methoxy-9,10-anthraquinone

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