61295-52-1

Usage

InChI:InChI=1/C7H13ClO/c1-3-5-7(9)6(8)4-2/h6H,3-5H2,1-2H3

Upstream product

• 123-19-3 4-heptanone 
• 61892-25-9 (E)-4-(trimethylsilyl)-3-heptene 

Downstream Products

• 62108-71-8 2-chloro-butyric acid propyl ester 
• 135307-45-8 c-2,c-3-diethyl-1-methoxy-c-3-methyl-r-1-cyclopropylbenzoat 

Relevant academic research and scientific papers

Theoretical and experimental studies on the Baeyer-Villiger oxidation of ketones and the effect of α-halo substituents

The Baeyer-Villiger reactions of acetone and 3-pentanone, including their fluorinated and chlorinated derivatives, with performic acid have been studied by ab initio and DFT calculations. Results are compared with experimental findings for the Baeyer-Villiger oxidation of aliphatic fluoro and chloroketones. According to theoretical results, the first transition state is rate-determining for all substrates even in the presence of acid catalyst. Although the introduction of acid into the reaction pathway leads to a dramatic decrease in the activation energy for the first transition state (TS), once entropy is included in the calculations, the enthalpic gain is lost. Of all substrates examined, pentanone reacts with performic acid via the lowest energy transition state. The second transition state is also lowest for pentanone, illustrating the accelerating effect of the additional alkyl group. Interestingly, there is only a small energetic difference in the transition states leading to migration of the fluorinated substituent versus the alkyl substituent in fluoropentanone and fluoroacetone. These differences match remarkably well with the experimentally obtained ratios of oxidation at the fluorinated and nonfluorinated carbons in a series of aliphatic ketones (calculated, 0.3 kcal/mol, observed, 0.5 kcal/mol), which are reported herein. The migration of the chlorinated substituent is significantly more difficult than that of the alkyl, with a difference in the second transition state of approximately 2.6 kcal/mol.

Metal-Catalyzed Organic Photoreactions. The Photooxidation of Vinylsilanes and Vinyl Sulfides in the Presence of Iron(III) Chloride, and the Regioselective Synthesis of α-Chloro Ketones

The irradiation of a pyridine solution of vinylsilanes or vinyl sulfides in the presence of iron(III) chloride under oxygen produced α-chloro ketones, with a carbonyl group at the olefinic carbon originally bearing a silicon or sulfur atom.

2-Mercaptocyclododecanone-1

The fruity flavor of a foodstuff is augmented or enhanced by the use of one or more α-oxy(oxo)mercaptans having the formula: STR1 wherein X is one of: STR2 or STR3 and R1 and R2, taken separately, are the same and are either of methyl, ethyl, 1-propyl or 2-propyl, or R1 and R2 taken together, is nonylene having the structure: STR4 said α-oxy(oxo)mercaptan being selected from the group consisting of: 3-mercapto-4-heptanol; 4-mercapto-5-nonanol; 4-mercapto-5-nonanone; 3-mercapto-2,6-dimethyl-4-heptanone; 2-mercaptocyclododecanone-1; and 2-mercapto-3-pentanone These compounds augment or enhance the green, grapefruit, fruity, buchu leaf oil-like, floral, green vegetable and/or minty aromas and grapefruit-like, green, citrus, bitter, lemon, buchu leaf oil-like, blackcurrant-like, green vegetable-like, and/or cooling notes of food flavors.

α-Oxy(oxo) sulfides and ethers

Described are α-oxy(oxo) sulfides and ethers having the generic structure: STR1 wherein X is one of: STR2 Z is one of sulfur or oxygen; when R1 and R2 are taken separately, R1 is hydrogen or methyl, and R2 is methyl; and when R1 and R2 are taken together, R1 and R2 form phenyl moieties; and Y is one of C1 -C4 alkyl, C3 or C4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl. Addition of one or more α-oxy(oxo) sulfides and ethers to foodstuff flavorings or foodstuffs is indicated to produce the following aroma and flavor characteristics, in the alternative or taken together: Aroma Green/spicey, Sweet, Fruity, Fresh/fruity, Gooseberry, Concord grape, Grape, Almond, Nutty, Cereal-like, Lachrymatory onion-like, Oniony, Green onion-like, Leek, Broccoli-like, Grapefruit, Celery stalk-like, Floral, Rosey, Woody, Blackcurrant, Buchu leaf oil-like, Citronellal-like, Neroli-like, Bergamot-like, Violet leaves-like, Jasmin-like, Melony, Cucumber-like, Green, Vegetable, Sweet/floral. Flavor Spicey, Sweet, Fruity, Milk caramel-like (dulce de leche-like), Gooseberry, Broccoli-like, Nutty, Cereal-like, Oniony, Grape, Concord grape, Citrusy, Grapefruit-like, Green fruit-like, Mandarin-like, Petitgrain-like, Blackcurrant, Minty, Astringent, Coriander-like, Green, Piney, Citronellal-like, Violet leaves-like, Melony, Green fruit-like, Cucumber, Green, Floral, Floral/green, Vegetable, Garlic With lasting mouthfeel and with, in many cases, an oniony aftertaste. The compounds of our invention are useful in augmenting or enhancing the flavor and aroma nuances of berry flavors, cereal-like flavors, nut flavors, broccoli flavors, onion flavors, citrus flavors (including neroli, bergamot, lime), jasmin flavors, grapefruit flavors, concord grape flavors, blackcurrant flavors, milk caramel flavors (e.g., dulce de leche-like flavors), vegetable flavors, cucumber flavors, celery flavors and spice flavors. Addition of a number of these α-oxy(oxo) sulfides and ethers in perfumes, colognes or perfumed articles imparts thereto sweet, green, floral, herbal, vegetative, basil-like, minty, melony, grapefruit, fruity and alliaceous aromas with yara, neroli and/or verdima-like nuances.