Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-

Base Information

• Chemical Name: Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-
• CAS No.: 738-72-7
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363
• Mol file: 738-72-7.mol

Synonyms:Streptimidon;Streptoimidone;NSC 66645;BRN 0033734;Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-;3-(2-Hydroxy-7-methyl-5-methylen-4-oxo-6-nonenyl)-glutarimid [German];3-(2-Hydroxy-7-methyl-5-methylen-4-oxo-6-nonenyl)-glutarimid;2,6-Piperidinedione, 4-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-, (R-(R*,S*-(E)))-;C16H23NO4;2,6-Piperidinedione, 4-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-;LS-115221

Chemical Property of Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-

Chemical Property:

• Vapor Pressure: 1.98E-12mmHg at 25°C
• Boiling Point: 507.6°Cat760mmHg
• Flash Point: 260.8°C
• PSA: 83.47000
• Density: 1.104g/cm³
• LogP: 1.84660
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 293.16270821
• Heavy Atom Count: 21
• Complexity: 451

Purity/Quality:

95% ^*data from raw suppliers

Streptimidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=C(C)C=C)C(=O)CC(CC1CC(=O)NC(=O)C1)O
• Isomeric SMILES: CC(/C=C(\C)/C=C)C(=O)CC(CC1CC(=O)NC(=O)C1)O

Technology Process of Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)-

There total 7 articles about Glutarimide, 3-(2-hydroxy-5,7-dimethyl-4-oxo-6,8-nonadienyl)- 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:

(2RS,3S)-4-benzyloxy-3-methylbutan-2-ol → streptimidone (738-72-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: DMAP; Et₃N / dimethylformamide / 10 h / 20 °C

2.1: H₂ / Pd-C / ethanol / 12 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -10 °C

4.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -70 °C

4.2: HMPA / hexane; tetrahydrofuran / 0.17 h

5.1: TBAF / tetrahydrofuran / 12 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

7.1: LiN(iPr)2 / tetrahydrofuran / 0.08 h / -70 °C

7.2: tetrahydrofuran / 0.5 h

With dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrogenolysis / 3.1: Swern oxidation / 4.1: deprotonation / 4.2: olefination / 5.1: Elimination / 6.1: Dehydrogenation / 7.1: enolation / 7.2: aldolisation;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

Reference yield:

(2S,3RS)-1-benzyloxy-3-tert-butyldimethylsilyloxy-2-methylbutane → streptimidone (738-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / Pd-C / ethanol / 12 h / 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -10 °C

3.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -70 °C

3.2: HMPA / hexane; tetrahydrofuran / 0.17 h

4.1: TBAF / tetrahydrofuran / 12 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

6.1: LiN(iPr)2 / tetrahydrofuran / 0.08 h / -70 °C

6.2: tetrahydrofuran / 0.5 h

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Hydrogenolysis / 2.1: Swern oxidation / 3.1: deprotonation / 3.2: olefination / 4.1: Elimination / 5.1: Dehydrogenation / 6.1: enolation / 6.2: aldolisation;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

Reference yield:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde (2066-88-8) + (3S)-3,5-dimethylhepta-4,6-dien-2-one (312728-63-5) → streptimidone (738-72-7) + 4-[(2'S,5'S,6'E)-2'-hydroxy-5',7'-dimethyl-4'-oxonona-6',8'-dienyl]piperidine-2,6-dione

Guidance literature:

(3S)-3,5-dimethylhepta-4,6-dien-2-one; With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.0833333h;

(2,6-dioxo-piperidin-4-yl)-acetaldehyde; In tetrahydrofuran; for 0.5h;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

upstream raw materials:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde

(3S)-3,5-dimethylhepta-4,6-dien-2-one

Downstream raw materials:

pyruvaldehyde bis-(2,4-dinitro-phenylhydrazone)