Preparation and Odour Properties of (<i>S</i>)-3-Mercapto-1-Heptyl Acetate

Sun, Baoguo; Yang, Shaoxiang; Liu, Yongguo; Tian, Hongyu; Liu, Yuping; Chen, Haitao

doi:10.3184/174751914x13989627250405

Cited by 4 publications

(1 citation statement)

References 25 publications

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“…1,2-Epoxy-4-heptanol was converted to 1,2-epithio-4-heptanol by treatment with thiourea in the presence of Ti(OPr i ) 4 according to the procedure in our previous work. 13 1,2-Epithio-4-heptanol was obtained in 80% yield as a mixture of two diastereoisomers with a ratio of 56/44, which was also determined by GC and confirmed by 1 H and 13 C NMR spectral data (Table 1). Obviously the conversion was stereospecific and the ratio of the two diastereoisomers of episulfide was in line with that of the epoxide.…”

Section: Resultsmentioning

confidence: 59%

Synthesis of a New Odourant, 2-Mercapto-4-Heptanol

Yang

Gong

Sun

et al. 2015

Journal of Chemical Research

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2-Mercapto-4-heptanol is a relatively new flavour compound that was recently approved as an ingredient by the Flavour and Extract Manufacturers' Association in 2013. Its synthesis, which we have accomplished in four-steps, involved firstly a Grignard reaction of n-butanal with allylmagnesium chloride to prepare 1-hepten-4-ol. This was epoxidised and then converted to 1,2-epithio-4-heptanol, reduction of which with LiAlH 4 gave the target compound in an overall yield of about 54%.

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Section: Resultsmentioning

confidence: 59%

Synthesis of a New Odourant, 2-Mercapto-4-Heptanol

Yang

Gong

Sun

et al. 2015

Journal of Chemical Research

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ChemInform Abstract: Preparation and Odor Properties of (S)‐3‐Mercapto‐1‐heptyl Acetate.

et al. 2014

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Preparation and Odor Properties of (S)-3-Mercapto-1-heptyl Acetate. -A stereoselective synthesis of the title compound ((S)-XI) is presented. The corresponding enantiomer can be prepared by using (R,R)-diethyl tartrate instead of (S,S)-diethyl tartrate in the Sharpless epoxidation step. Target compound ((S)-XI) possesses a tropical fruit aroma. -(LIANG, S.; SUN, B.; YANG, S.; LIU, Y.; TIAN*, H.; LIU, Y.; CHEN, H.; J. Chem. Res. 38 (2014) 6, 343-346, http://dx.doi.org/10.3184/174751914X13989627250405 ; Sch. Chem. Food, Beijing Technol. Bus. Univ., Beijing 100048, Peop. Rep. China; Eng.) -M. Bohle 51-069

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Enantioselective synthesis and sensory properties of 3‐methylthiodecanal

Jiang

Líu

Liu

et al. 2017

Flavour & Fragrance J

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The enantioselective synthesis of two enantiomers of 3‐methylthiodecanal was described, in which the optically active 1‐undecen‐4‐ols prepared by asymmetric catalytic addition of n‐octanal with allyltributylstannane went through oxidation of double bond and nucleophilic substitution of hydroxy group via mesylate to afford the target molecules with about 90% ee values. Odour properties and approximate thresholds were determined by means of GC/Olfactory. The data indicated that two enantiomers of 3‐methylthiodecanal presented distinctive odour feature from each other and also a slight difference in odour intensity.

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Preparation and Odour Properties of (S)-3-Mercapto-1-Heptyl Acetate

Cited by 4 publications

References 25 publications

Synthesis of a New Odourant, 2-Mercapto-4-Heptanol

Synthesis of a New Odourant, 2-Mercapto-4-Heptanol

ChemInform Abstract: Preparation and Odor Properties of (S)‐3‐Mercapto‐1‐heptyl Acetate.

Enantioselective synthesis and sensory properties of 3‐methylthiodecanal

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