2-(2,5-dimethylphenyl)-1-hydroxy-8-methoxy-4-azaspiro[4.5]dec-1-en-3-one

Base Information

• Chemical Name: 2-(2,5-dimethylphenyl)-1-hydroxy-8-methoxy-4-azaspiro[4.5]dec-1-en-3-one
• CAS No.: 203312-38-3
• Molecular Formula: C18H23NO3
• Molecular Weight: 301.386
• Mol file: 203312-38-3.mol

Synonyms:spirotetramat-enol;Spirotetramat Metabolite BYI08330-cis-enol;cis-3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one;cis-3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one solution;

Chemical Property of 2-(2,5-dimethylphenyl)-1-hydroxy-8-methoxy-4-azaspiro[4.5]dec-1-en-3-one

Chemical Property:

• Vapor Pressure: 1.07E-11mmHg at 25°C
• Boiling Point: 521.4oC at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 269.1oC
• PSA: 62.05000
• Density: 1.2g/cm3
• LogP: 3.30600
• Storage Temp.: ?20°C

Purity/Quality:

99% ^*data from raw suppliers

Spirotetramat Metabolite BYI08330-cis-enol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 51/53-57
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(2,5-dimethylphenyl)-1-hydroxy-8-methoxy-4-azaspiro[4.5]dec-1-en-3-one

There total 5 articles about 2-(2,5-dimethylphenyl)-1-hydroxy-8-methoxy-4-azaspiro[4.5]dec-1-en-3-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: 91.1%

methyl cis-1-[2-(2,5-dimethylphenyl)acetamido]-4-methoxycyclohexane-1-carboxylate (203313-47-7) → cis-3-(2,5-dimethylphen yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one (203312-38-3)

Guidance literature:

methyl cis-1-[2-(2,5-dimethylphenyl)acetamido]-4-methoxycyclohexane-1-carboxylate; With sodium methylate; In N,N-dimethyl-formamide; at 20 - 30 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In water; at 40 ℃; for 0.333333h;

DOI:10.1134/S1070428020100176

Reference yield:

4-methoxycyclohexanone (13482-23-0) → cis-3-(2,5-dimethylphen yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one (203312-38-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water / 15 h / 50 °C

2.1: calcium hydroxide; water / 45 h / 95 °C

3.1: thionyl chloride / 10 h / Reflux

4.1: potassium carbonate / water; ethyl acetate / 0 - 25 °C

5.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 20 - 30 °C / Inert atmosphere

5.2: 0.33 h / 40 °C

With thionyl chloride; water; sodium methylate; potassium carbonate; calcium hydroxide; In water; ethyl acetate; N,N-dimethyl-formamide; 1.1: |Bucherer-Bergs Reaction / 5.1: |Dieckmann Condensation / 5.2: |Dieckmann Condensation;

DOI:10.1134/S1070428020100176

Reference yield:

cis-8-methoxy-1,3-diazaspiro[4.5]decane-2,4-dione (387825-48-1) → cis-3-(2,5-dimethylphen yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one (203312-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: calcium hydroxide; water / 45 h / 95 °C

2.1: thionyl chloride / 10 h / Reflux

3.1: potassium carbonate / water; ethyl acetate / 0 - 25 °C

4.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 20 - 30 °C / Inert atmosphere

4.2: 0.33 h / 40 °C

With thionyl chloride; water; sodium methylate; potassium carbonate; calcium hydroxide; In water; ethyl acetate; N,N-dimethyl-formamide; 4.1: |Dieckmann Condensation / 4.2: |Dieckmann Condensation;

DOI:10.1134/S1070428020100176

upstream raw materials:

methyl cis-1-[2-(2,5-dimethylphenyl)acetamido]-4-methoxycyclohexane-1-carboxylate

4-methoxycyclohexanone

cis-8-methoxy-1,3-diazaspiro[4.5]decane-2,4-dione

cis-1-amino-4-methoxycyclohexane-1-carboxylic acid

Downstream raw materials:

spirotetramat

Refernces

• 1、 Yao, Ting-Ting,Cheng, Jing-Li,Xu, Bing-Rong,Zhang, Min-Zhe,Hu, Yong-Zhou,Zhao, Jin-Hao,Dong, Xiao-Wu. "Support vector machine (SVM) classification model based rational design of novel tetronic acid derivatives as potent insecticidal and acaricidal agents". . p. 49195 - 49203. Retrieved 2015.