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1128-08-1

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1128-08-1 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1128-08-1 differently. You can refer to the following data:
1. 2-Pentyl-3-methyl-2-cyclopenten-1-one is a colorless, slightly viscous liquid with a typical jasmine odor, resembling that of the naturally occurring (Z)-jasmone. Dihydrojasmone is produced by an acid-catalyzed rearrangement of 4-methyl-??-decalactone, which is readily obtained by radical addition of 2-octanol to acrylic acid. Dihydrojasmone is used in perfumery in jasmine bases and, more generally, in floral and fruity fragrances.
2. 3-Methyl-2-(n-pentanyl)-2-cyclopenten-1-one has a fresh, fruity, jasmine odor with woody and herbal nuances.

Occurrence

Has apparently not been reported to occur in nature.

Preparation

Hexyl bromide plus levulinic ester yields a lactone, which is reacted with polyphosphoric acid or phosphorus pentoxide to produce hydrojasmone.

Taste threshold values

Taste characteristics at 10 ppm: sweet, floral, green, herbal with a citrus nuance.

Synthesis Reference(s)

Canadian Journal of Chemistry, 56, p. 2301, 1978 DOI: 10.1139/v78-379Journal of the American Chemical Society, 92, p. 7428, 1970 DOI: 10.1021/ja00728a029

Check Digit Verification of cas no

The CAS Registry Mumber 1128-08-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1128-08:
(6*1)+(5*1)+(4*2)+(3*8)+(2*0)+(1*8)=51
51 % 10 = 1
So 1128-08-1 is a valid CAS Registry Number.

1128-08-1 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A19298)  Dihydrojasmone, 97%   

  • 1128-08-1

  • 25g

  • 356.0CNY

  • Detail
  • Alfa Aesar

  • (A19298)  Dihydrojasmone, 97%   

  • 1128-08-1

  • 100g

  • 580.0CNY

  • Detail
  • Sigma-Aldrich

  • (00138)  Dihydrojasmone  analytical standard

  • 1128-08-1

  • 00138-1ML

  • 522.99CNY

  • Detail

1128-08-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Pentyl-3-methyl-2-cyclopenten-1-one

1.2 Other means of identification

Product number -
Other names DihydrojasMone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1128-08-1 SDS

1128-08-1Relevant articles and documents

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Miyashita,M. et al.

, p. 4679 - 4681 (1976)

-

-

Stork,G.,Borch,R.

, p. 935 - 936 (1964)

-

2-METHYLENE-3-ALKOXYCYCLOPENTANONES AS REACTIVE INTERMEDIATES AND THEIR APPLICATION TO THE SYNTHESES OF DIHYDROJASMONE, CIS-JASMONE AND (+/-)-JASMOLONE

Takahashi, Takashi,Hori, Kimihiko,Tsuji, Jiro

, p. 1189 - 1192 (1981)

Dihydrojasmone and cis-jasmone were synthesized in high yields by the Michael addition of lithium di-n-butylcuprate and bromomagnesium di-1-butenylcuprate, respectively, to 2-methylene-3-methyl-3-methoxy-methyloxycyclopentanone. (+/-)-Jasmolone was also synthesized by the Michael addition of dialkenylcuprate to 2-methylene-3-methyl-3-methoxymethyloxy-4-ethoxyethyloxycyclopentanone.

Utilization of Basic Alumina in a One-Pot Synthesis of 1,4-Diketones, 1,4,7-Triketones, and Dihydrojasmone by Conjugate Addition of Nitroalkanes to Enones

Ballini, Roberto,Petrini, Marino,Marcantoni, Enrico,Rosini, Goffredo

, p. 231 - 233 (1988)

The one-pot synthesis of functionalized 1,4-diketones was achieved in good yields by conjugate addition of primary nitroalkanes to α,β-unsaturated carbonyl compounds on basic alumina without solvent, followed by in situ oxidation with 30percent aqueous hydrogen peroxide in methanol.The one-pot syntheses of 1,4,7-triketones and dihydrojasmone are also reported.

-

Bellassoued,M. et al.

, p. 35 - 38 (1979)

-

Simple one-step synthesis of 1,4-diketones: A new approach to dihydrojasmone

Pecunioso,Menicagli

, p. 2614 - 2617 (1988)

-

Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

Erden, Ihsan,?cal, Nüket,Song, Jiangao,Gleason, Cindy,G?rtner, Christian

, p. 10676 - 10682 (2006)

An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2Cl2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2.

Dessau,Heiba

, p. 3457 (1974)

A SIMPLE SYNTHESIS OF DIHYDROJASMONE

Liu, Shing-Hou

, p. 439 - 440 (1983)

Acetalization of a γ-substituted α,β-unsaturated ketone, followed by acid hydrolysis gave a cyclopentenone.

Guaciaro et al.

, p. 4661 (1978)

Herrmann,J.L. et al.

, p. 3275 - 3278 (1973)

-

Murata,S.,Matsuda,I.

, p. 221 - 222 (1978)

-

α,β-Unsaturated ketones via copper(II) bromide mediated oxidation

Sharley, James S.,Collado Pérez, Ana María,Ferri, Estela Espinos,Miranda, Amadeo Fernandez,Baxendale, Ian R.

, p. 2947 - 2954 (2016)

A protocol for effecting a rapid Saegusa-type oxidation of enol acetates is reported. This new method relies on the in situ elimination of an α-bromo intermediate to generate α,β-unsaturated ketones using copper(II) bromide. The methodology developed was applied to a range of substrates including a cyclohexanone, which could be directly converted to the corresponding phenol derivative. A catalytic system in which a non-masked ketone was successfully oxidised using substoichiometric CuBr2 was also developed as a proof of principle.

A Novel Acetonylation of Carbonucleophiles via Palladium-Catalyzed Allylation with Isopropyl 2-Methylene-3,5-dioxahexyl Carbonate

Ikeda, Isao,Gu, Xue-Ping,Okuhara, Toshio,Okahara, Mitsuo

, p. 32 - 34 (1990)

Carbonucleophiles such as malonate esters, β-keto esters, phenylacetate ester, and phenylacetonitrile were acetonylated in high yields by allylation with isopropyl (or methyl) 2-methylene-3,5-dioxahexyl carbonate (4b or 4a) in the presence of palladium-phosphine catalyst under neutral conditions, followed by acidic hydrolysis.Adopting this procedure dihydrojasmone (7) was prepared from ethyl 3-oxononanoate (6) in an overall yield of 72percent.

A New Synthesis of Vinyl Sulphides by Lewis Acid Promoted Reaction of trimethylsilanes with Trisubstituted Alkenes

Ishibashi, Hiroyuki,Nakatani, Hiroshi,Sakashita, Hiroshi,Ikeda, Masazumi

, p. 338 - 340 (1987)

Treatment of the α0chloro-α-silyl sulphides (1) or (5) with trisubstituted alkenes (6) in the presence of SnCl4 gave the vinyl sulphides (7) or (8), the formation of which involves a carbenium ion rearrangement controlled by the silyl group.

Ruzicka,Pfeiffer

, p. 1208,1214 (1933)

Photo-Fries-type rearrangement of cyclic enamides. An efficient route to structurally diverse five-membered enaminones

Furman, Bart?omiej,Szcze?niak, Piotr

, p. 1898 - 1901 (2022/02/19)

A simple, efficient and user-friendly protocol for the preparation of structurally diverse enaminones from enamides has been developed. The strategy is based on a photo-induced intramolecular Fries-type rearrangement. The photochemical transformation proceeds under mild reaction conditions, applies to a broad substrate range, is highly economic, and limits the amount of waste produced. The proposed methodology was used as a key step in the synthesis of dihydrojasmone an important fragrance compound.

Synthesis method of dihydrojasmonone

-

Paragraph 0040-0047, (2021/07/31)

The invention discloses a synthesis method of dihydrojasmonone, belongs to the technical field of perfume synthesis, aims to solve the problems that raw materials are difficult to prepare and high in price, and the fragrance of a product is impure, and relates to a method for synthesizing dihydrojasmonone by reacting halogenated n-hexane and magnesium chips under a solvent condition to generate an n-hexyl Grignard reagent under anhydrous and nitrogen protection, carrying out catalytic coupling on the n-hexyl Grignard reagent and acetyl propionyl chloride through vanadium trichloride to generate undecane-2,5-dione, and carrying out condensation ring closing on undecane-2,5-dione under an alkaline condition. In the synthesis route, the used raw materials are cheap and easy to obtain, and other auxiliary reagents are all industrial basic raw materials, so that the price is low; reaction steps are short, and reaction conditions are simple; and in addition, the reaction yield is relatively high and is kept at 64-72%, and the purity is relatively high and is kept at about 98%, so that the method is suitable for realizing industrial production and has relatively high application value.

Method for synthesizing dihydrojasmone under alkaline condition

-

Paragraph 0026-0035, (2020/11/12)

The invention discloses a method for synthesizing dihydrojasmone under an alkaline condition, which comprises the following steps of: adding alkali liquor into a reaction kettle provided with a mechanical stirrer, a water segregator and a reflux condenser pipe, uniformly stirring, heating, refluxing, dropwise adding methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate into a reaction kettle at the dropwise adding rate of 12-15 g/min, then carrying out a reaction process for 4-6 h under the reflux condition of 80-100 DEG C, carrying out standing and layering so that an organic phase 1 is obtained after a water phase is separated out, adding a sodium sulfate aqueous solution into the organic phase 1, stirring for 10-30 minutes, standing for layering, separating out a water phase to obtain an organic phase 2, carrying out reduced pressure distillation on the organic phase 2, and collecting fractions to obtain dihydrojasmones. Compared with the traditional process, the synthetic method has the advantages that the reaction conditions are simple, the dihydrojasmones can be synthesized under common heating reflux conditions, the synthetic steps are simple and convenient, the yield of the dihydrojasmones prepared by the synthetic method is high, and the purity of the prepared dihydrojasmones is high and can reach 99.5%.

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