𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Novel Synthesis of 3,5,5-Trimethyl-4-(2-butenylidene)-cyclohex-2-en-1-one, a Major Constituent of Burley Tobacco Flavour

✍ Scribed by Edouard Demole; Paul Enggist

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
303 KB
Volume
57
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The acetylenic diol 2, prepared by reaction of but‐3‐yn‐2‐ol dianion with 2,6,6‐trimethyl‐4,4‐ethylenedioxy‐cyclohex‐2‐en‐1‐one (1), afforded 3,5,5‐trimethyl‐4‐(2‐butenylidene)‐cyclohex‐2‐en‐1‐one (4), a major constituent of Burley tobacco flavour, upon LiAlH~4~ reduction and hydrolysis. Vomifoliol (5) and blumenol C (6) were major by‐products in this reaction.

📜 SIMILAR VOLUMES

A Chemical Study of Burley Tobacco Flavo
A Chemical Study of Burley Tobacco Flavour (Nicotiana tabacum L.). III. Structure Determination and Synthesis of 5-(4-Methyl-2-furyl)-6-methylheptan-2-one (“Solanofuran”) and of 3,4,7-Trimethyl-1,6- dioxa-spiro[4.5]dec-3-en-2-one (“Spiroxabovolide”), Two New Flavour Components of Burley Tobacco
✍ E. Demole; Mrs C. Demole; D. Berthet 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 396 KB 👁 1 views

## Abstract Two novel constituents of __Burley__ tobacco condensate were shown to be 5‐(4‐methyl‐2‐furyl)‐6‐methylheptan‐2‐one (__solanofuran__, **4**) and 3,4,7‐trimethyl‐1,6‐dioxa‐spiro[4.5]‐dec‐3‐en‐2‐one (__spiroxabovolide__, **6**). These structures were deduced from spectral data and confirme

A Chemical Study of Burley Tobacco Flavo
A Chemical Study of Burley Tobacco Flavour (Nicotiana tabacumL.) V. Identification and Synthesis of the Novel Terpenoid Alkaloids 1, 3, 6, 6-Tetramethyl-5, 6, 7, 8-tetrahydro-isoquinolin-8-one and 3, 6, 6-Trimethyl-5,6-dihydro-7H-2-pyrindin-7-one
✍ Edouard Demole; Cécile Demole 📂 Article 📅 1975 🏛 John Wiley and Sons 🌐 German ⚖ 601 KB

## Abstract GLC. allowed the isolation of 1, 3, 6, 6‐tetramethyl‐5, 6, 7, 8‐tetrahydro‐isoquinolin‐8‐one (__A__) and 3,6,6‐trimethyl‐5,6‐dihydro‐__7H__‐2‐pyrindin‐7‐one (__D__) from __Burley__ tobacco condensate (about 0.1% each). The structures and syntheses of these novel terpenoid alkaloids are