103383-83-1

Basic information

• Product Name: 5-Hexen-2-one, 3-hydroxy-3-methyl-, (+)- (9CI)
• CAS NO: 103383-83-1
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 0
• Product Categories: ACETYLGROUP
• Mol File: 103383-83-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Hexen-2-one, 3-hydroxy-3-methyl-, (+)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexen-2-one, 3-hydroxy-3-methyl-, (+)- (9CI)(103383-83-1)
• EPA Substance Registry System: 5-Hexen-2-one, 3-hydroxy-3-methyl-, (+)- (9CI)(103383-83-1)

Safety Data

• Hazardous Substances Data: 103383-83-1(Hazardous Substances Data)

Upstream product

• 431-03-8 dimethylglyoxal 
• 1730-25-2 allylmagnesium bromide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 106-95-6 allyl bromide 
• 64549-05-9 allyldibutyltin chloride 
• 42082-94-0 3-<(trimethylsilyl)oxy>-3-buten-2-one 

Downstream Products

• 502848-52-4 benzoic acid-5-allyl-5-methyl-4-oxo-4,5-dihydrofuran-3-ylmethylester 
• 128939-11-7 2-[(E)-Benzylimino]-3-methyl-hex-5-en-3-ol 

Relevant articles and documents

Total synthesis and stereochemical assignment of (-)-ushikulide A

We report the determination of the full stereostructure of (-)-ushikulide A (1), a spiroketal containing macrolide by total synthesis. Ushikulide A (1) was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin (2), a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallography. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asymmetric alkynylation of a simple saturated aldehyde with methyl propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.

Novel reactions of indium reagents with 1,2-diones: A facile synthesis of α-hydroxy ketones

Indium mediated reactions of allyl, cinnamyl, propargyl and benzyl bromides, ethyl bromoacetate and ethyl-4-bromocrotonate with 1,2-diones, in the presence of sodium iodide, occur efficiently to afford α-hydroxy keto compounds in excellent yields.

Allylstannation of α-, β-and γ-diketones mediated by allylbutyltin halides: Bu2(CH2=CHCH2)SnCl and Bu(CH2=CHCH2) SnCl2

Butane-2,3-(1a), pentane-2,4-(1b) and hexane-2,5-dione (1c) react with Bu2(CH2=CHCH2)SnCl in the presence of water to give monoallylated keto-ols (2a, 2b) and/or diallylated diols (3a, 3b, 3c), this depending upon the employed molar ratio [diketone]/[allyltin chloride]. Bu(CH2=CHCH2)SnCl2 reacts with neat 1c in a one-pot synthesis to give mixtures of heterocyclic compounds: 2,5-diallyl-2,5-dimethyltetrahydrofuran (4), and 3-chloro-1,5-dimethyl-8-oxabicyclo [3,2,1] octane (5). Compound 4 is also obtained in high yield from the corresponding diol 3c by cyclodehydration promoted by RSnCl3 (R = Me and Bu).