(-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone

Base Information

• Chemical Name: (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone
• CAS No.: 78829-11-5
• Molecular Formula: C₁₇H₂₄N₂O₂S
• Molecular Weight: 320.456
• Mol file: 78829-11-5.mol

Synonyms:(-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone

Chemical Property of (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone

There total 11 articles about (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone 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%

(+)-trans-(2R)-bromo-(5R)-tert-butylcyclohexanone p-toluenesulfonylhydrazone (78829-10-4) → triethylamine hydrobromide (636-70-4) + (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone (78829-11-5) + C17H24N2O2S (78964-93-9)

Guidance literature:

With triethylamine; In benzene; for 0.5h; Yield given. Title compound not separated from byproducts;

DOI:10.1021/ja00408a007

Reference yield: 64.0%

(5R)-tert-butylcyclohex-1-enyl p-toluenesulfonylazine (78939-29-4) → (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone (78829-11-5)

Guidance literature:

With triethylamine; In benzene; for 0.25h;

DOI:10.1021/ja00408a007

Reference yield:

3-tert-butylphenyol (585-34-2) → (-)-(5R)-tert-butylcyclohex-2-enone p-toluenesulfonylhydrazone (78829-11-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / H₂ / 5percent Rh/C / methanol

2: 89 percent / CrO₃-H₂SO₄ / acetone

3: 1.) LiAlH₄, 2.) pyridine / 1.) Et₂O

4: 1.) brucine / 2.) saponification

5: 94 percent / Jones reagent

6: 1.) lithium diisopropylamide, 2) Me₃SiCl, 3.) Br₂ / 1.) THF, -78 deg C, 25 min, 2.) RT, 20 min, 3.) CCl₄, -15 deg C, 15 min

7: 79 percent / diethyl ether / 0 deg C -> RT

8: 99 percent / NaHCO₃ / diethyl ether; H₂O / 0.05 h / 0 °C

9: 64 percent / Et₃N / benzene / 0.25 h

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; jones reagent; sulfuric acid; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; brucine; lithium diisopropyl amide; Rh on carbon; In methanol; diethyl ether; water; acetone; benzene;

DOI:10.1021/ja00408a007

upstream raw materials:

(5R)-tert-butylcyclohex-1-enyl p-toluenesulfonylazine

(+)-trans-(2R)-bromo-(5R)-tert-butylcyclohexanone p-toluenesulfonylhydrazone

3-tert-butylphenyol

3-tert-butylcyclohexanol

Downstream raw materials:

(+)-(5R)-tert-butyl-3-deuterio-1,3-cyclohexadiene

(+)-(5R)-tert-butyl-1,3-cyclohexadiene