(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

Base Information

• Chemical Name: (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one
• CAS No.: 1346681-71-7
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 1346681-71-7.mol

Synonyms:(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

Chemical Property of (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

Chemical Property:

• Melting Point: 75-77°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1E)-4-Hydroxy-1-mesityl-4-methylpent-1-en-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: The following hydroxamic acid was shown by Bode and coworkers to assist in the kinetic resolution of cyclic amines through acylation of one enantiomer, which can be controlled using either the (R,S)- or (S,R)-Bode Kinetic Resolution Catalyst, both of which are also available through Sigma-Aldrich.

Technology Process of (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

There total 1 articles about (1E)-4-hydroxy-1-mesityl-4-methylpent-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: 51.0%

mesytaldehyde (487-68-3) + 3-Hydroxy-3-methyl-2-butanone (115-22-0) → (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one (1346681-71-7)

Guidance literature:

With lithium hydroxide; In methanol; water; at 80 ℃; for 18h;

DOI:10.1021/ja209472h

Reference yield: 88.0%

(4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one (1346681-70-6) + (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one (1346681-71-7) → (4aR,9aS)-4-[(3-mesitylpropanoyl)oxy]-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one (1346682-03-8)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 23 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ja209472h

Reference yield: 50.0%

6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (4118-36-9) + (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one (1346681-71-7) → (1S)-2-(3-mesitylpropanoyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinoline (1346682-00-5) + (R)-(+)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (178032-64-9)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 23 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Resolution of racemate;

DOI:10.1021/ja209472h

upstream raw materials:

mesytaldehyde

3-Hydroxy-3-methyl-2-butanone

Downstream raw materials:

benzyl (2R)-2-methylazepane-1-carboxylate

(2S)-1-(3-mesitylpropanoyl)-2-methylazepane

benzyl (3R)-3-methylmorpholine-4-carboxylate

(3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine

Refernces

• 1、 Binanzer, Michael,Hsieh, Sheng-Ying,Bode, Jeffrey W.. "Catalytic kinetic resolution of cyclic secondary amines". supporting information; experimental part. p. 19698 - 19701. Retrieved 2012/01/13.