(-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-one

Base Information

• Chemical Name: (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-one
• CAS No.: 674781-50-1
• Molecular Formula: C₂₁H₂₆OS
• Molecular Weight: 326.503

Synonyms:(-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-one

Chemical Property of (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-one

There total 11 articles about (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.0^1,6]dodec-7-en-10-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: 85.0%

(+)-phenylselenyl [(4aS,8R,8aS)-7-phenylthio-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate (674781-49-8) → (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.01,6]dodec-7-en-10-one (674781-50-1)

Guidance literature:

With bis(tri-n-butyltin); In benzene; for 4h; Irradiation;

DOI:10.1021/ol0363063

Reference yield:

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol (166022-29-3) → (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.01,6]dodec-7-en-10-one (674781-50-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: Mg / tetrahydrofuran

2.2: tetrahydrofuran / 0.5 h / 0 °C

2.3: 2.5 g / HMPA / tetrahydrofuran / 0 - 20 °C

3.1: 57 percent / PPh₃; AcOH / Pd(OAc)2 / 760 Torr / Heating

4.1: 92 percent / K₂CO₃ / acetone / 4 h / 20 °C

5.1: 78 percent / aq. NaOH; benzyltriethylammonium chloride; MeOH / CH₂Cl₂ / 8 h / 20 °C

6.1: 99 percent / 1,1,1,3,3,3-hexafluoro-2-propanol; NaHCO₃ / 4 h / 20 °C

7.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

8.1: 100 percent / aq. NaOH / H₂O / 6 h / Heating

9.1: Et₃N; PhOP(O)Cl₂ / tetrahydrofuran / 1 h / 0 °C

9.2: 71 percent / Et₃N / tetrahydrofuran / 0.5 h / 0 °C

10.1: 85 percent / (Bu₃Sn)2 / benzene / 4 h / Irradiation

With methanol; sodium hydroxide; oxalyl dichloride; 1,1,1,3',3',3'-hexafluoro-propanol; N-benzyl-N,N,N-triethylammonium chloride; bis(tri-n-butyltin); sodium hydrogencarbonate; potassium carbonate; magnesium; acetic acid; dimethyl sulfoxide; O-phenyl phosphorodichloridate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; water; acetone; benzene; 1.1: Swern oxidation;

DOI:10.1021/ol0363063

Reference yield:

(S)-(+)-2',2'-dimethyl-6'-methylene-1'-cyclohexylcarboxaldehyde (166022-30-6) → (-)-(1S,6S,9S)-8-phenylthio-5,5,9-trimethyltricyclo[7.2.1.01,6]dodec-7-en-10-one (674781-50-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Mg / tetrahydrofuran

1.2: tetrahydrofuran / 0.5 h / 0 °C

1.3: 2.5 g / HMPA / tetrahydrofuran / 0 - 20 °C

2.1: 57 percent / PPh₃; AcOH / Pd(OAc)2 / 760 Torr / Heating

3.1: 92 percent / K₂CO₃ / acetone / 4 h / 20 °C

4.1: 78 percent / aq. NaOH; benzyltriethylammonium chloride; MeOH / CH₂Cl₂ / 8 h / 20 °C

5.1: 99 percent / 1,1,1,3,3,3-hexafluoro-2-propanol; NaHCO₃ / 4 h / 20 °C

6.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

7.1: 100 percent / aq. NaOH / H₂O / 6 h / Heating

8.1: Et₃N; PhOP(O)Cl₂ / tetrahydrofuran / 1 h / 0 °C

8.2: 71 percent / Et₃N / tetrahydrofuran / 0.5 h / 0 °C

9.1: 85 percent / (Bu₃Sn)2 / benzene / 4 h / Irradiation

With methanol; sodium hydroxide; 1,1,1,3',3',3'-hexafluoro-propanol; N-benzyl-N,N,N-triethylammonium chloride; bis(tri-n-butyltin); sodium hydrogencarbonate; potassium carbonate; magnesium; acetic acid; O-phenyl phosphorodichloridate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; water; acetone; benzene;

DOI:10.1021/ol0363063

upstream raw materials:

(+)-phenylselenyl [(4aS,8R,8aS)-7-phenylthio-1,1,6-trimethyl-8-(4-methoxyphenylsulfonyl)-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-yl]acetate

(S)-(+)-2',2'-dimethyl-6'-methylene-1'-cyclohexylcarboxaldehyde

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

(1S)-(+)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylic acid

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