cis-12-nor-Carophyll-5-en-2-on | 60362-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-12-nor-Carophyll-5-en-2-on
• 英文别名: 8-Oxo-4,11,11-trimethylbicyclo<7.2.0>undec-4-en；(1S,5Z,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-5-en-2-one
• CAS: 60362-45-0
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: MBZBBVTYLUNZPJ-JUYDSFNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-12-nor-Carophyll-5-en-2-on 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 (1S,2Z,5Z,9R)-2,6,10,10-tetramethylbicyclo<7.2.0>undeca-2,5-diene
  参考文献：
  名称：

  Rearrangement of (-)-.beta.-Caryophyllene. A Product Analysis and Force Field Study

  摘要：

  The rearrangement of (-)-beta-caryophyllene (1) with sulfuric acid in ether has been reinvestigated. In the early stage, a multitude of products is formed. Of these, fourteen hydrocarbons (3, 4, 6-17) and four alcohols (5, 18-20) were obtained pure. From the very beginning, the tricycloundecenes 15-17 accumulate quickly. This indicates that a previously unknown rearrangement of 1 by protonation of the exocyclic double bond followed by transannular ring closure is a main reaction, and that the conformation beta alpha is involved. Three hydrocarbons (3, 4, 8) and three alcohols (5, 18, 19) proved to be stable. They are the main components in the late stage. A complete rearrangement scheme followed from a force field analysis using MMP2. First, all conformations up to 4 kcal above the global minimum of each product and each carbenium ion necessary for its formation were detected automatically using the search program HUNTER. Second, the conformation favoring a specific transformation was searched for. For transannular cyclizations, the conformation with the shortest distance between the atoms to be bound and, for ring openings and 1,2-shifts, the conformation with the smallest dihedral angle between the empty p-orbital and the bond to be broken were selected. In all cases, the selection criteria proved valid: The stereochemistry of the conformations selected matched the stereochemistry of the products observed. On the basis of the results presented, a fully automated search prog ram for favorable rearrangement paths may be developed.

  DOI：

  10.1021/ja00141a009

文献信息

• [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。
• METHODS FOR REPELLING INSECTS USING SESQUITERPENE HYDROCARBONS AND THEIR DERIVATIVES
  申请人：Zhang Qinghe

  公开号：US20100166896A1

  公开（公告）日：2010-07-01

  Methods for repelling flying or biting insects from an area, a human, or an animal subject are provided. The methods include treating the area, or applying to a subject or to a device worn by the subject seychellene, α-guaiene, and α-bulnesene, or a mixture thereof. Additional compounds including β-caryophyllene, isocaryophyllene, β-caryophyllene oxide, β-caryophyllene ketone, α-humulene, β-patchoulene, α-patchoulene, β-elemene, (+)-longipinene, (−)-isolongifolene, (+)-longifolene, and linalool, clove oil, and/or patchouli oil may also be used.
• US8057829B2
  申请人：——

  公开号：US8057829B2

  公开（公告）日：2011-11-15