シクロペンタデカノン

化学的特性Cyclopentadecanone is a musk fragrance found in the scent gland of the male civet cat. A number of syntheses have been developed for its manufacture [260]. Among these, the so-called Story procedure is the only route that has the potential to make cyclopentadecanone available on a larger scale, but due to the handling of hydroperoxides, the process is difficult to manage. The process starts from tricyclohexylidene triperoxide, which is obtained by oxidation of cyclohexanone with hydrogen peroxide. Pyrolysis leads to a mixture of 1,16-hexadecanolide and cyclopentadecane. The latter is oxidized by oxygen under boric acid catalysis to cyclopentadecanol, which is subsequently oxidized to cyclopentadecanone. Due to the availability of long-chained aliphatic dicarboxylic acids by biotechnological processes, a Dieckmann condensation reaction may also possibly be a useful route to produce this macrocyclic ketone. Cyclopentadecanone is used in fine fragrances：

化学性质持続性のある強いムスク香

解説C15H28O(224.39)．ノルムスコンともいう．シクロペンタデカノン, 雄のジャコウ猫のジャコウ腺から分泌される香気性化合物．合成法が多数報告されているが，たとえば，ヘキサデカンジカルボン酸ナトリウム塩を減圧下で加熱乾留すると得られる．融点65～66 ℃，沸点142～144 ℃(400 Pa)．d66"0.897．n66"1.464．3-メチルシクロペンタデカノンであるムスコンとよく似た香気を有し，ともに高級香料に利用される．森北出版「化学辞典（第2版）

天然物の起源Reported to be found in the scent glands of the Louisiana muskrat Ondatra zibethicus rivalicius (Guenther, 1949).

使用Cyclopentadecanone is the main odoriferous component of musk.

製造方法By the cyclization of dinitriles in high dilution (Bedoukian. 1967).

合成方法大環状ムスク

純化方法Subliming Exaltone is better than crystallising it from aqueous EtOH for purification. The semicarbazone has m 186-187o. [Stevens & Erickson J Am Chem Soc 64 146 1942, Mathur et al. J Chem Soc 3505 1963, Biens & Hess Helv Chim Acta 71 1704 1988, Beilstein 7 III 203, 7 IV 118.]