(1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one

Base Information

• Chemical Name: (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one
• CAS No.: 76757-79-4
• Molecular Formula: C₁₈H₁₉IO₂S
• Molecular Weight: 426.318

Synonyms:(1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one

Chemical Property of (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one

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Technology Process of (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one

There total 4 articles about (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-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: 93.0%

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid (76757-75-0) → (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.01,5]dodec-4-en-11-one (76757-79-4)

Guidance literature:

With iodine; sodium hydrogencarbonate; potassium iodide; In water; for 20h;

DOI:10.1021/jo00322a017

Reference yield:

N-(phenylthio)succinimide (14204-24-1) → (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.01,5]dodec-4-en-11-one (76757-79-4)

Guidance literature:

Multi-step reaction with 4 steps

1: LiBF₄ / tetrahydrofuran / 1 h / -30 °C

2: 1.) KH / 1.) THF, room temp., 10 min, 2.) reflux, 3 d

3: 90 percent / 10percent aq. NaOH / 20 h / Heating

4: 93 percent / I₂/KI, NaHCO₃ / H₂O / 20 h

With sodium hydroxide; lithium tetrafluoroborate; iodine; potassium hydride; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; water;

DOI:10.1021/jo00322a017

Reference yield:

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester (76773-01-8) → (1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.01,5]dodec-4-en-11-one (76757-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 10percent aq. NaOH / 20 h / Heating

2: 93 percent / I₂/KI, NaHCO₃ / H₂O / 20 h

With sodium hydroxide; iodine; sodium hydrogencarbonate; potassium iodide; In water;

DOI:10.1021/jo00322a017

upstream raw materials:

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid

N-(phenylthio)succinimide

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester

1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat

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