(6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone

Base Information

• Chemical Name: (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone
• CAS No.: 162301-60-2
• Molecular Formula: C₁₉H₂₆N₂O₂S
• Molecular Weight: 346.494
• Mol file: 162301-60-2.mol

Synonyms:(6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone

Chemical Property of (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone

There total 21 articles about (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone 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: 97.0%

(6S,7S)-6,10-dimethylbicyclo[5.3.0]dec-1(10)-en-2-one (136374-67-9) + toluene-4-sulfonic acid hydrazide (1576-35-8) → (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone (162301-60-2)

Guidance literature:

With hydrogenchloride; In methanol; for 4h; Ambient temperature;

Reference yield:

(1S,5S,6S,9R)-5,9-dimethylbicyclo<4.3.0>non-3-ene-2,8-dione (162211-24-7) → (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone (162301-60-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 43 percent / NaBH₄ / methanol / 2 h / 0 °C

2: 95 percent / H₂ / 10percent palladium on carbon / ethyl acetate / 5 h / Ambient temperature

3: 98 percent / PPh₃, DEAD / tetrahydrofuran / 2 h / Ambient temperature

4: 10percent aq. NaOH / methanol

5: 1.) BF₃*Et₂O, 2.) NaCl / 1.) ether, room temperature, 12 h, 2.) DMSO, H₂O, 170 deg C, 4 h

6: 89 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

7: 1.) silica gel, 2.) DBU / 1.) room temperature, 12 h, 2.) Et₂O, room temperature, 5 h

8: 97 percent / etheral HCl / methanol / 4 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

Reference yield:

(3'R,3'aS,7'S,7'aS)-3',7'-Dimethyl-3',3'a,7',7'a-tetrahydro-1'H-spiro[[1,3]dioxolane-2,2'-inden]-4'-one (137141-20-9) → (6S,7S)-6,10-dimethylbicyclo<5.3.0>dec-1(10)-en-2-one toluene-p-sulfonylhydrazone (162301-60-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / 70percent HClO₄ / acetone / 5 h / Ambient temperature

2: 43 percent / NaBH₄ / methanol / 2 h / 0 °C

3: 95 percent / H₂ / 10percent palladium on carbon / ethyl acetate / 5 h / Ambient temperature

4: 98 percent / PPh₃, DEAD / tetrahydrofuran / 2 h / Ambient temperature

5: 10percent aq. NaOH / methanol

6: 1.) BF₃*Et₂O, 2.) NaCl / 1.) ether, room temperature, 12 h, 2.) DMSO, H₂O, 170 deg C, 4 h

7: 89 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

8: 1.) silica gel, 2.) DBU / 1.) room temperature, 12 h, 2.) Et₂O, room temperature, 5 h

9: 97 percent / etheral HCl / methanol / 4 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; perchloric acid; boron trifluoride diethyl etherate; hydrogen; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; sodium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone;

upstream raw materials:

(6S,7S)-6,10-dimethylbicyclo[5.3.0]dec-1⁽¹⁰⁾-en-2-one

toluene-4-sulfonic acid hydrazide

(3'R,3'aS,7'S,7'aS)-3',7'-Dimethyl-3',3'a,7',7'a-tetrahydro-1'H-spiro[[1,3]dioxolane-2,2'-inden]-4'-one

(1S,5S,6S,9R)-5,9-dimethylbicyclo<4.3.0>non-3-ene-2,8-dione

Downstream raw materials:

(-)-1αH,10αH-tri-nor-guaia-4,6-diene

Refernces

• 1、 Asaoka, Morio,Kosaka, Takatoshi,Itahana, Hirotsune,Takei, Hisashi. "Total Synthesis of Clavukerin A and Its Epimer". . p. 1295 - 1298. Retrieved 2007/10/02.