4-Hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one

Base Information

• Chemical Name: 4-Hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one
• CAS No.: 148476-30-6
• Molecular Formula: C17H20 O3
• Molecular Weight: 272.344
• Mol file: 148476-30-6.mol

Synonyms:4-Hydroxy-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4.4]non-3-en-2-one

Chemical Property of 4-Hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one

Chemical Property:

• Vapor Pressure: 5.56E-10mmHg at 25°C
• Melting Point: approximate 253℃ (dec.)
• Refractive Index: 1.592
• Boiling Point: 478.9°C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 203.8°C
• PSA: 46.53000
• Density: 1.2g/cm³
• LogP: 3.75050

Purity/Quality:

97% ^*data from raw suppliers

3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-ol(SpiromesifenMetaboliteM01) ^*data from reagent suppliers

Safty Information:

• Statements: 52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-ol, is the metabolite of Spiromesifen, which is a Spirocyclic Tetronic Acid, environmentally friendly and novel structural pesticide.

Technology Process of 4-Hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-one

There total 6 articles about 4-Hydroxy-3-mesityl-1-oxaspiro(4.4)non-3-en-2-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: 85.0%

2-mesitylacetic acid (4408-60-0) + hydroxycyclopentanecarboxylic acid ethyl ester (41248-23-1) → 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4,4]indole-3-en-4-ol (148476-30-6)

Guidance literature:

2-mesitylacetic acid; hydroxycyclopentanecarboxylic acid ethyl ester; With trichlorophosphate; In toluene; at 20 ℃;

With sodium hydroxide; In toluene; for 8h; Reflux;

Reference yield:

1-[2-(2,4,6-Trimethyl-phenyl)-acetoxy]-cyclopentanecarboxylic acid ethyl ester (361366-15-6) → 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4,4]indole-3-en-4-ol (148476-30-6)

Guidance literature:

With potassium tert-butylate;

DOI:10.2533/000942903777678588

Reference yield:

1-hydroxy-cyclopentanecarboxylic acid (16841-19-3) → 3-(2,4,6-trimethylphenyl)-2-oxo-1-oxaspiro[4,4]indole-3-en-4-ol (148476-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH

2: KOtBu

With potassium tert-butylate; toluene-4-sulfonic acid;

DOI:10.2533/000942903777678588

upstream raw materials:

1-[2-(2,4,6-Trimethyl-phenyl)-acetoxy]-cyclopentanecarboxylic acid ethyl ester

1-hydroxy-cyclopentanecarboxylic acid

1-hydroxycyclopentanecarbonitrile

hydroxycyclopentanecarboxylic acid ethyl ester

Downstream raw materials:

C₂₃H₂₇NO₅

C₂₉H₃₃NO₅

C₂₇H₂₈BrNO₅

C₂₄H₂₉NO₅

Refernces

• 1、 Liu, Zhihui,Lei, Qiong,Li, Yongqiang,Xiong, Lixia,Song, Haibin,Wang, Qingmin. "Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety". scheme or table. p. 12543 - 12549. Retrieved 2012/03/10.