(10R)-8-methyl-10-[(2R)-6-methylhept-5-en-2-yl]-4-phenyl-2,4,6-triazatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione | 1443410-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (10R)-8-methyl-10-[(2R)-6-methylhept-5-en-2-yl]-4-phenyl-2,4,6-triazatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione
• CAS: 1443410-85-2
• 化学式: C₂₃H₂₉N₃O₂
• 分子量: 379.502
• InChiKey: FJVMZQJHTNDZSE-ZBRPZPHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 在 吡啶 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 26.5h， 生成 (10R)-8-methyl-10-[(2R)-6-methylhept-5-en-2-yl]-4-phenyl-2,4,6-triazatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione 、 (6R,7R)-(-)-1,3(15),10-bisabolatriene
  参考文献：
  名称：

  Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (Halyomorpha halys) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols

  摘要：

  We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.

  DOI：

  10.1021/np5003753

文献信息

• US9451771B2
  申请人：——

  公开号：US9451771B2

  公开（公告）日：2016-09-27