195251-91-3

Basic information

• Product Name: 7-tert-butyl-1,5-benzodioxepin-3(4h)-one
• Synonyms: 7-tert-butyl-1,5-benzodioxepin-3(4h)-one;2H-1,5-Benzodioxepin-3(4H)-on, 7-(1,1-dimethylethyl)-
• CAS NO: 195251-91-3
• Molecular Formula: C13H16O3
• Molecular Weight: 220.26434
• EINECS: 424-860-5
• Mol File: 195251-91-3.mol

Chemical Properties

• Boiling Point: 323.271°C at 760 mmHg
• Flash Point: 140.354°C
• Appearance: /
• Density: 1.105g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 7-tert-butyl-1,5-benzodioxepin-3(4h)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-tert-butyl-1,5-benzodioxepin-3(4h)-one(195251-91-3)
• EPA Substance Registry System: 7-tert-butyl-1,5-benzodioxepin-3(4h)-one(195251-91-3)

Safety Data

• Hazardous Substances Data: 195251-91-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H16O3/c1-13(2,3)9-4-5-11-12(6-9)16-8-10(14)7-15-11/h4-6H,7-8H2,1-3H3

Upstream product

• 944558-51-4 2,2'-{[4-(tert-butyl)-1,2-phenylene]bis(oxy)}bis[acetic acid] dimethyl ester 
• 98-29-3 4-tert-Butylcatechol 
• 944558-71-8 7-(tert-butyl)-3,4-dihydro-3-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1,5-benzodioxepine 
• 534-07-6 1,3-Dichloroacetone 

Relevant articles and documents

Synthesis of benzodioxepinone analogues via a novel synthetic route with qualitative olfactory evaluation

Marine odorants represent a minor yet diverse class of substances within the fragrance industry, of which 7-methyl-2H-1,5-benzodioxepin-3(4H)-one (1) is commercially known as Calone 1951, a synthetic first in the area of marine-fragrance chemistry. To determine the extent to which the characteristic marine odor of Calone 1951 corresponds to the substitution at the benzo portion of the molecule, a variety of aromatic substituents were incorporated into the benzodioxepinone structure (Scheme 1, Table 3). In light of the difficulty experienced in applying patented literature to deriving the analogues 12-18, particularly those with electron-withdrawing substituents, an alternative synthetic scheme was implemented for the construction of all analogues in favorable yields (Scheme 4, Table 3). Formation of the hydroxy-protected dihalo alkylating agent 24 via epoxide cleavage of epichlorohydrin (Scheme 3) allowed etherification favoring dihalo displacement and subsequent intramolecular ring closure (-→26a-g). THP Deprotection followed by oxidation of the alcohols 27a-g to the ketones 12-18 provided a general pathway to the benzodioxepinone products. The influence of the substituent nature on odor activity revealed a diverse scope of olfactory character (Table 4).

Structure-activity relationship in the domain of odorants having marine notes

We synthesized or re-synthesized a large series of 2H-1,5-benzodioxepin- 3(4H)-ones 9 (Scheme 1), 4,5-dihydro-1-benzoxepin-3(2H)-ones 10 (Schemes 3 and 4) and 5,6,8,9-tetrahydro-7H-benzocyclohepten-7-ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well-known benzodioxepinone named Calone 1951 (9b). We meticulously described the odor profile of each synthesized compound and discussed relevant structure-odor relationships (Tables 1-3). In particular, we revealed a correlation between the conformation of the seven-membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.