4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

Base Information

• Chemical Name: 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one
• CAS No.: 158469-57-9
• Molecular Formula: C₂₄H₂₂O₄S
• Molecular Weight: 406.502
• Mol file: 158469-57-9.mol

Synonyms:4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

Chemical Property of 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

There total 11 articles about 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-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: 94.0%

4-Methoxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.13,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one (158469-54-6) → 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.13,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one (158469-57-9)

Guidance literature:

With aluminum tri-bromide; ethanethiol; In dichloromethane; for 1h;

DOI:10.1021/jo00097a052

Reference yield:

4-bromobenzenecarbonitrile (623-00-7) → 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.13,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one (158469-57-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / K₂CO₃, CuO, pyridine / 21 h / 120 °C

2: 80 percent / H₅IO₆, I₂, aq. H₂SO₄ / acetic acid / 2 h / 90 °C

3: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 7 h / -78 °C

4: 94 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran; toluene / 1.) -78 deg C, 10 min, 2.) -78 deg C, 10 h

5: 94 percent / DBU / tetrahydrofuran / 30 h / Heating

6: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 1.) -78 deg, 2 h, 2.) ice-bath cooling, 30 min

7: 79 percent / Pd(OAc)2 / various solvent(s) / 1.) r.t., 30 min, 2.) 25 deg C, 40 h

8: 97 percent / 2 N aq. NaOH / methanol / 3 h / Ambient temperature

9: 89 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 20 h / Ambient temperature

10: 94 percent / AlBr₃, ethanethiol / CH₂Cl₂; various solvent(s) / 1 h

With pyridine; palladium diacetate; sodium hydroxide; aluminum tri-bromide; 18-crown-6 ether; sulfuric acid; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; triphenylphosphine; ethanethiol; copper(II) oxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; acetic acid; toluene;

DOI:10.1021/jo00097a052

Reference yield:

4-(2'-methoxyphenoxy)benzonitrile (78338-67-7) → 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.13,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one (158469-57-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / H₅IO₆, I₂, aq. H₂SO₄ / acetic acid / 2 h / 90 °C

2: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 7 h / -78 °C

3: 94 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran; toluene / 1.) -78 deg C, 10 min, 2.) -78 deg C, 10 h

4: 94 percent / DBU / tetrahydrofuran / 30 h / Heating

5: 99 percent / DIBAL-H / diethyl ether; cyclohexane / 1.) -78 deg, 2 h, 2.) ice-bath cooling, 30 min

6: 79 percent / Pd(OAc)2 / various solvent(s) / 1.) r.t., 30 min, 2.) 25 deg C, 40 h

7: 97 percent / 2 N aq. NaOH / methanol / 3 h / Ambient temperature

8: 89 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 20 h / Ambient temperature

9: 94 percent / AlBr₃, ethanethiol / CH₂Cl₂; various solvent(s) / 1 h

With palladium diacetate; sodium hydroxide; aluminum tri-bromide; 18-crown-6 ether; sulfuric acid; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; triphenylphosphine; ethanethiol; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; acetic acid; toluene;

DOI:10.1021/jo00097a052

upstream raw materials:

4-Methoxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one

4-bromobenzenecarbonitrile

4-(2'-methoxyphenoxy)benzonitrile

2-methoxy-phenol

Downstream raw materials:

combretastatin D-2