chichimol ketone | 915105-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chichimol ketone
• 英文别名: 4-methyl-1-hepten-3-one；4-(S)-methyl-1-hepten-3-one；(S)-4-Methyl-1-hepten-3-one；(4S)-4-methylhept-1-en-3-one
• CAS: 915105-71-4
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: FMZDFRXBZBPNSU-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  chichimol ketone 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以99%的产率得到(S)-(+)-4-甲基-3-庚酮
  参考文献：
  名称：

  Synthesis and absolute configuration of (S)-(+)-chichimol ketone: the defensive secretion of walking stick Agathemera elegans

  摘要：

  The first enantioselective synthesis of chichimol ketone (4-methyl-1-hepten-3-one) is described and the absolute configuration of the main semiochemical compound is determined as having an (S)-configuration. The synthesis features the use of a ruthenium catalytic asymmetric hydrogenation reaction to introduce chirality into acid 2. The synthetic chichimol ketone (S)-1 displayed a specific rotation that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural chichimol ketone. To assure the correct stereochemical assignment, (S)-1 was converted in the known ketone (S)-5: the main alarm pheromone of the ant Atta texana that is 400 times more active than its (R)enantiomers. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.030
• 作为产物：
  描述：

  乙烯基溴化镁 、 (2S)-N-methoxy-N,2-dimethylpentanamide 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到chichimol ketone
  参考文献：
  名称：

  Synthesis and absolute configuration of (S)-(+)-chichimol ketone: the defensive secretion of walking stick Agathemera elegans

  摘要：

  The first enantioselective synthesis of chichimol ketone (4-methyl-1-hepten-3-one) is described and the absolute configuration of the main semiochemical compound is determined as having an (S)-configuration. The synthesis features the use of a ruthenium catalytic asymmetric hydrogenation reaction to introduce chirality into acid 2. The synthetic chichimol ketone (S)-1 displayed a specific rotation that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural chichimol ketone. To assure the correct stereochemical assignment, (S)-1 was converted in the known ketone (S)-5: the main alarm pheromone of the ant Atta texana that is 400 times more active than its (R)enantiomers. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.030