3301-90-4

Basic information

• Product Name: 6-ethyltetrahydro-2H-pyran-2-one
• Synonyms: 6-ethyltetrahydro-2H-pyran-2-one;2H-Pyran-2-one, 6-ethyltetrahydro-;HEPTANO-1,5-LACTONE;5-Hydroxyheptanoic acid lactone;Einecs 221-972-4;Hepta-1,5-lactone;Delta-Heptalactone
• CAS NO: 3301-90-4
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.16898
• EINECS: 221-972-4
• Mol File: 3301-90-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 227 °C at 760 mmHg
• Flash Point: 85.6 °C
• Appearance: /
• Density: 0.974 g/cm³
• Vapor Pressure: 0.0795mmHg at 25°C
• Refractive Index: 1.431
• CAS DataBase Reference: 6-ethyltetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ethyltetrahydro-2H-pyran-2-one(3301-90-4)
• EPA Substance Registry System: 6-ethyltetrahydro-2H-pyran-2-one(3301-90-4)

Safety Data

• Hazardous Substances Data: 3301-90-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 47, 1976 DOI: 10.1016/S0040-4039(00)71319-0

InChI:InChI=1/C7H12O2/c1-2-6-4-3-5-7(8)9-6/h6H,2-5H2,1H3

Upstream product

• 88071-66-3 (+/-)-Oct-7-en-3-ol 
• 628-62-6 heptanamide 
• 64847-88-7 2-ethylcyclopentanone 
• 1462-96-0 1-ethylcyclopentanol 
• 120-92-3 cyclopentanone 
• 1119-60-4 hept-6-enoic acid 
• 3637-13-6 5-oxoheptanoic acid 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 1345692-63-8 1,5-di-(tert-butyldimethylsilyloxy)heptane 
• 2146-38-5 1-ethylcyclopentene 
• 74327-34-7 5-oxoheptanal 
• 22935-13-3 2-ethyl-1,6-hexanedioic acid 
• 111-14-8 oenanthic acid 
• 6225-10-1 N-methylpentanamide 

Downstream Products

• 111-14-8 oenanthic acid 
• 483287-70-3 (R)-(-)-5-fluoroheptyl benzoate 
• 38847-12-0 (S)-7-hydroxy-1-((S)-1-phenyl-ethylamino)-nonan-3-one (S)-cyclohemiacetal 

Relevant articles and documents

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METHOD OF SYNTHESIS

Described is a method of synthesizing 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0] octan-3-one by reacting 3-(5-ethoxyhept-1-yl) cyclopentene with dichloroketene. The resulting reaction products are reacted with acetic acid and zinc to produce 4-(5-ethoxyhept-1 -yl)bicyclo[3.2.0]heptan-6-one and 4-(5-ethoxyhept-1-yl)bicyclo [3.2.0]heptan-7-one, which are reacted with trimethylsulfonium iodide to produce 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2'-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0]heptane-6,2'-oxirane]. Lithium iodide is reacted with 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2'-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0]heptane-6,2'-oxirane] to produce 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one. A method of synthesizing 6-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-3-one is also described.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.