4,10,10-trimethyl-7-methylene-1β,8α-bicyclo[6.2.0]decene-4-carboxaldehyde | 475285-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 4,10,10-trimethyl-7-methylene-1β,8α-bicyclo[6.2.0]decene-4-carboxaldehyde
• 英文别名: (1R,9S)-4-formyl-8-methylene-4,11,11-trimethylbicyclo<6,2,0>decane；4,10,10-Trimethyl-7-methylen-bicyclo<6.2.0>decan-4-aldehyd；(1R,8S)-4,10,10-trimethyl-7-methylidenebicyclo[6.2.0]decane-4-carbaldehyde
• CAS: 475285-25-7
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: PGESEZMTIVWZDC-HCYNLOQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Caryophyllene oxide 以 苯 为溶剂， 生成 4,10,10-trimethyl-7-methylene-1β,8α-bicyclo[6.2.0]decene-4-carboxaldehyde
  参考文献：
  名称：

  Nigam,I.C.; Levi,L., Journal of Organic Chemistry, 1965, vol. 30, p. 653 - 654

  摘要：

  DOI：

文献信息

• Rearranged caryophyllenes by biotransformation with Chaetomium cochliodes
  作者：Wolf-Rainer Abraham、Ludger Ernst、Hans-Adolf Arfmann

  DOI：10.1016/0031-9422(90)80013-7

  日期：——

  Abstract Biotransformation of caryophyllene by Chaetomium cochliodes DSM 1909 (=ATCC 10195) leads to 4,5-epoxy-caryophyllene-7,12-diol as the main product. The hydroxylation of the geminal methyl groups is not very stereospecific, but as with Diploida gossypina the main product possesses the 11 R -configuration. Side-reactions are ring contraction or formation of clovanes, probably via epoxide rearrangements

  摘要 Chaetomium cochliodes DSM 1909 (=ATCC 10195) 对石竹烯进行生物转化，主要产物为 4,5-epoxy-caryophyllene-7,12-diol。孪生甲基的羟基化不是很立体，但与棉二倍体一样，主要产物具有 11 R-构型。副反应是环收缩或形成丁二酮，可能是通过环氧化物重排。使用单或双环氧石竹烯作为底物不会显着增加产率。相反，双环氧-石竹烯产生了一种斑点蛋白衍生物。在棉双孢菌的发酵产物中观察到相同的分子框架，但具有不同的构型，这支持石竹烷是此类抗生素的前体的假设。
• [EN] PROCESS FOR PREPARING 1-[(1R,4R/S,8S)-10,10-DIMETHYL-7-METHYLENE-4-BICYCLO[6.2.0]DECANYL]ETHANONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 1-[(1R,4R/S,8S)-10,10-DIMÉTHYL-7-MÉTHYLÈNE-4-BICYCLO[6.2.0]DÉCANYL]ÉTHANONE
  申请人：BASF SE

  公开号：WO2016097239A1

  公开（公告）日：2016-06-23

  The present invention relates to a process for preparing 1-[(1R,4R/S,8S)-10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decanyl]ethanone.

  本发明涉及一种制备1-[(1R,4R/S,8S)-10,10-二甲基-7-亚甲基-4-双环[6.2.0]癸烷基]乙酮的方法。
• [EN] 1-(7,10,10-TRIMETHYL-4-BICYCLO(6.2.0)DECANYL)ETHANONE AS NOVEL AROMA CHEMICAL<br/>[FR] 1-(7,10,10-TRIMÉTHYL-4-BICYCLO(6.2.0)DÉCANYL)ÉTHANONE COMME NOUVEL AGENT CHIMIQUE AROMATIQUE
  申请人：BASF SE

  公开号：WO2016097238A1

  公开（公告）日：2016-06-23

  The present invention relates to -(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone, the use of 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone as a fragrance or as flavor, to a method for imparting or modifying a scent or a flavor to a composition by including said compound into such composition, to a fragrance containing composition and/or a fragrance material containing said compound and to a process for preparing 1-(7,10,10-trimethyl-4-bicyclo[6.2.0]decanyl)ethanone.

  本发明涉及-(7,10,10-三甲基-4-双环[6.2.0]癸烷基)乙酮，以1-(7,10,10-三甲基-4-双环[6.2.0]癸烷基)乙酮作为香料或味道的用途，通过将该化合物加入到该组成物中来赋予或改变气味或味道的方法，包括含有该化合物的香料组成物和/或香料材料，以及制备1-(7,10,10-三甲基-4-双环[6.2.0]癸烷基)乙酮的方法。
• Synthesis and oxidation of sulfides based on (–)-caryophyllene oxide and tert-butanethiol
  作者：J. W. Gyrdymova、E. S. Izmest´ev、S. A. Rubtsova、A. V. Kutchin

  DOI：10.1007/s11172-016-1441-9

  日期：2016.5

  An acid-catalyzed reaction of (–)-caryophyllene oxide with tert-butanethiol led to sulfides with the clovane structure of the sesquiterpene fragment in up to 63% yields. The oxidation of these sulfides gave sulfoxides in up to 38% yields (de 59%) and sulfones in up to 89%.

  (-)-石竹烯氧化物与叔丁硫醇的酸催化反应导致硫化物具有倍半萜烯片段的丁二烯结构，产率高达 63%。这些硫化物的氧化产生高达 38% 的亚砜（de 59%）和高达 89% 的砜。
• ——
  作者：L. E. Tatarova、D. V. Korchagina、V. A. Barkhash

  DOI：10.1023/a:1016595005735

  日期：——

  Products of reaction between caryophyllene 4beta,5alpha-epoxide and carbonyl compounds (acrolein, crotonaldehyde, alpha-methacrolein, and acetone) were synthesized on clay. Two diastereomers in reaction with each aldehyde and a single isomer with acetone were obtained. In reaction of the epoxide with acetone an isomerization product was isolated, 4,4,9-trimethyltricyclo[6.2.2.0(1.5)]dodec-9-en-2beta-ol that was unknown before.