Dihydrojasmone

Structural formula
General
Surname	Dihydrojasmone
other names	2-pentyl-3-methyl-2-cyclopenten-1-one
Molecular formula	C 11 H 18 O
Brief description	colorless liquid
External identifiers / databases
CAS number 1128-08-1 EC number 214-434-5 ECHA InfoCard 100.013.122 PubChem 62378 ChemSpider 56166 Wikidata Q1225162
properties
Molar mass	166.26 g · mol -1
Physical state	liquid
density	0.916 g cm −3 (25 ° C)
boiling point	120-121 ° C (12 mmHg)
solubility	almost insoluble in water, soluble in ethanol
Refractive index	1.4767 (20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Dihydrojasmone is one of jasmone derived chemical compound . It is a colorless liquid with a characteristic smell that is used in perfumes as an odorous substance (jasmine-like).

presentation

The synthesis of dihydrojasmone was first described by Heinz Hunsdiecker in 1942 . In the Hunsdiecker condensation , 2,5-undecanedione is cyclized in boiling ethanol with 2 percent aqueous sodium hydroxide solution as a catalyst .

Cyclization of 2,5-undecanedione to dihydrojasmone

2,5-Undecanedione can be obtained by cleaving 2-hexyl- 5-methylfuran , which can be obtained from 5-methylfurfural in a multi-stage reaction sequence with poor yield . An alternative process for the production of 2,5-undecanedione starts from n - heptanal , whereby the carbonyl group is protected with 1,3-propanedithiol as dithiane . After alkylation and cleavage of the protective group , the starting compound for the dihydrojasmone synthesis is obtained.

A technically simple synthesis of dihydrojasmone starts from n- heptylamine , which is oxidized with ozone at −78 ° C to 1-nitroheptane . This is dissolved in chloroform and reacted with catalytic amounts of diisopropylamine at 40 ° C. with methyl vinyl ketone and then evaporated to dryness with basic silica gel and converted to the end product at 80 ° C. for 48 hours.

Synthesis of dihydrojasmone from n -heylamine and methyl vinyl ketone

Alternative synthesis routes use 2-methylfuran or methyl acrylate as the starting component .

Individual evidence

1. ↑ ^{a b c d e f} Data sheet Dihydrojasmone, ≥98%, stabilized, FG from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).
2. ↑ data sheet at TheGoodScents
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-366.
4. ↑ ^{a b} Heinz Hunsdiecker: About the behavior of γ-diketones, 1st communication . In: Reports of the German Chemical Society . tape 75 , no. 5 , May 6, 1942, pp. 447-454 , doi : 10.1002 / cber.19420750502 .
5. ↑ Patent US2387587 : Process of manufacturing cyclopentenone derivatives. Registered on August 20, 1940 , published October 23, 1945 , inventor: Heinz Hunsdiecker. ‌
6. ↑ External identifiers or database links for 5-methylfurfural : CAS number: 620-02-0, EC number: 210-622-6, ECHA InfoCard: 100.009.658 , GESTIS substance database : 493494 , PubChem : 12097 , ChemSpider : 11600 , Wikidata : Q22830264 .
7. ↑ Tse-Lok Ho, Honor C. Ho, CM Wong: A Synthetic Route to Dihydrojasmone; Sulfuric Acid as Dethioacetalization Agent . In: Canadian Journal of Chemistry . 51 (2), 1973, pp. 153-155, doi : 10.1139 / v73-023 .
8. ^ Ehud Keinan, Yehuda Mazur: Reactions in dry media. A simple conversion of nitro groups into carbonyls . In: Journal of the American Chemical Society . tape 99 , no. March 11 , 1977, p. 3861 , doi : 10.1021 / ja00453a067 .
9. ↑ Janusz Nowicki: Review: Synthesis of Jasmonoides from Furan Derivatives , in: Molecules , 2000 , 5 , pp. 1201-1209.
10. ^ GW Parshall, WA Nugent, DM-T. Chan, W. Tam: A new role for organometallic reactions in organic synthesis in industry (PDF; 220 kB) , in: Pure Appl. Chem. , 1985 , 57  (12), pp. 1809-1818.