anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone

Base Information

• Chemical Name: anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone
• CAS No.: 80976-41-6
• Molecular Formula: C₁₅H₁₆N₂O₂S
• Molecular Weight: 288.37
• Mol file: 80976-41-6.mol

Synonyms:

Chemical Property of anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone

There total 7 articles about anti-bicyclo<3.2.1>octa-2,6-dien-4-one 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: 39.0%

bicyclo<3.2.1>octa-3,6-dien-2-one (1122-53-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → bicyclo<3.2.1>octa-3,6-dien-2-one tosylhydrazone (80976-41-6)

Guidance literature:

With pyridine; In methanol; for 8h; Ambient temperature;

DOI:10.1021/jo00132a011

Reference yield: 29.0%

bicyclo<3.2.1>oct-3-en-2-one (3212-77-9) + toluene-4-sulfonic acid hydrazide (1576-35-8) → bicyclo<3.2.1>oct-3-en-2-one p-toluenesulfonylhydrazone (80976-48-3) + anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone (80976-45-0,80997-16-6,80976-41-6)

Guidance literature:

In pyridine; at 0 ℃; for 288h;

DOI:10.1021/ja00373a022

Reference yield:

exo-bicyclo<3.2.1>oct-3-en-2-ol (4802-43-1,93628-29-6) → anti-bicyclo<3.2.1>octa-2,6-dien-4-one p-toluenesulfonylhydrazone (80976-45-0,80997-16-6,80976-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / CrO₃-pyridine / pyridine / 48 h / 0 - 5 °C

2: pyridine / 288 h / 0 °C

With chromium trioxide-pyridine complex; In pyridine;

DOI:10.1021/ja00373a022

upstream raw materials:

bicyclo<3.2.1>octa-3,6-dien-2-one

toluene-4-sulfonic acid hydrazide

3-bromobicyclo<3.2.1>octa-3,6-dien-2-ol

3,4-dibromobicyclo<3.2.1>octa-2,6-diene

Downstream raw materials:

bicyclo<3.2.1>octa-3,6-dien-2-one tosylhydrazone lithium salt

tetracyclo<3.3.0^2,8.0^4,6.0>octane

bicyclo<3.2.1>octa-2,6-diene

5-ethynyl-1,3-cyclohexadiene

Refernces

• 1、 Murahashi, Shun-Ichi,Okumura, Kazuo,Naota, Takeshi,Nagase, Shigeru. "Srtructure and Reactivity of Bicycloocta-2,6-dien-4-ylidene and Bicyclooct-2-en-4-ylidene. Nucleophilicity of Vinylcarbenes". . p. 2466 - 2475. Retrieved 2007/10/02.