(R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one
• 英文别名: (R)-1,3-dihydroxy-3,7-dimethyloct-6-en-2-one；(R)-3,7-dimethyl-2-oxo-oct-6-ene-1,3-diol；(R)-3,7-dimethyl-2-oxo-6-octene-1,3-diol；(3R)-1,3-dihydroxy-3,7-dimethyloct-6-en-2-one
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: FOMPNSJZRJXFMV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 (R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(R)-3-hydroxy-3,7-dimethyl-2-oxo-6-octenyl 4-bromobenzoate
  参考文献：
  名称：

  Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer

  摘要：

  An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethy1-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.018
• 作为产物：
  描述：

  [(2R,3S)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methyl acetate 在 4-二甲氨基吡啶 、 高氯酸 、 四丁基氟化铵 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 80.08h， 生成 (R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  Enzyme-assisted synthesis of (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle, and its (R)-enantiomer

  摘要：

  (S)-1,3-Dihydroxy-3,7-dimethyl-6-octen-2-one, the male-produced aggregation pheromone of the Colorado potato beetle (Leptinotarsa decemlineata), and its (R)-isomer were synthesized by employing lipase-catalyzed asymmetric acetylation of (+/-)-2,3-epoxynerol as the key step. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.030

文献信息

• Organic Synthesis in Pheromone Science
  作者：Kenji Mori

  DOI：10.3390/10091023

  日期：——

  Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are summarized to emphasize biodiversity as revealed in pheromone perception.

  给出了例子来说明化学和/或酶促不对称反应在合成宽角面粉甲虫、跳虫、黑加仑茎切割虫和科罗拉多土豆甲虫的新信息素中的应用。总结了信息素中立体化学与生物活性之间的关系，以强调在信息素感知中揭示的生物多样性。
• Alternative Synthesis of the Colorado Potato Beetle Pheromone
  作者：Juan A. Faraldos、Robert M. Coates、José-Luis Giner

  DOI：10.1021/jo4017056

  日期：2013.10.18

  involves a 6-endo epoxide ring-opening with ester participation that simultaneously inverts the 3R-configuration of the (3R)-2,3-epoxy-2-fluoroprenyl acetate intermediate and installs the ketone functionality of the semiochemical. Extensive NMR studies validate the proposed 6-endo mechanism of the featured rearrangement, which under anhydrous conditions resulted in the formation of two bicyclic 1,3-dioxan-5-ones

  雄性科罗拉多马铃薯甲虫分泌的信息素的简明制剂[即。(3 S )-1,3-二羟基-3,7-二甲基-6-辛烯-2-one]从2-氟橙花醇或2-氟香叶醇开始，分四步完成。合成中的关键步骤涉及酯参与的 6-内环氧化物开环，同时反转(3 R )-2,3-环氧-2-氟异戊二烯乙酸酯中间体的 3 R-构型并安装符号化学。广泛的 NMR 研究验证了所提出的特征重排的 6-endo 机制，该机制在无水条件下通过前所未有的分子内 Prins 环化形成两个双环 1,3-二恶烷-5-酮。
• Versatile Amine-Promoted Mild Methanolysis of 3,5-Dinitrobenzoates and Its Application to the Synthesis of Colorado Potato Beetle Pheromone
  作者：Yumiko Yamano、Haruna Sasaki、Akimori Wada

  DOI：10.1248/cpb.c17-00462

  日期：——

  A mild deacylation method for 3,5-dinitrobenzoates using methanolic solutions of amines, such as dialkylamines, was developed. The method's versatility was confirmed by applying it to synthesizing a key intermediate for Colorado potato beetle pheromone.

  开发了使用胺（例如二烷基胺）的甲醇溶液温和的3,5-二硝基苯甲酸酯脱酰方法。通过将该方法应用于科罗拉多马铃薯甲虫信息素的关键中间体的合成，证实了该方法的多功能性。
• (S)-3,7-Dimethyl-2-oxo-6-octene-1,3-diol: an aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata (Say)
  作者：James E Oliver、Joseph C Dickens、Thomas E Glass

  DOI：10.1016/s0040-4039(02)00349-0

  日期：2002.4

  (S)-3,7-Dimethyl-2-oxo-6-octene-1,3-diol has been identified as a male-produced pheromone from the Colorado potato beetle. Its gross structure was deduced from its mass and NMR spectra plus synthesis from geraniol. The absolute configuration was determined to be (S) by syntheses of both enantiomers from (R)- and (S)-linalool, respectively. Published by Elsevier Science Ltd.