(S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one | 443361-61-3

• 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: (S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
• 英文别名: (3S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-3,7-dimethyloct-6-en-2-one
• CAS: 443361-61-3
• 化学式: C₂₆H₃₆O₃Si
• 分子量: 424.656
• InChiKey: SNZCJXNPAQMSBA-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  从其降解产物合成科罗拉多马铃薯甲虫的聚集信息素

  摘要：

  将科罗拉多马铃薯甲虫聚集信息素（S）-1,3-二羟基-3,7-二甲基-6-辛烯-2-酮与该甲虫的触角或腿部提取物一起孵育，得到6-甲基-5-庚烯-二合一为主要产品。该酮用作信息素的立体选择性合成中的底物。将其以良好的立体选择性连接到乙醇酸的丁二缩醛上，并通过在硅胶上纯化该反应的产物来进一步富集所需的异构体。

  DOI：

  10.1016/j.bmcl.2015.06.083
• 作为产物：
  描述：

  (S)-芳樟醇 在 bis(acetylacetonate)oxovanadium 咪唑 、 叔丁基过氧化氢 、 高氯酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  (S)-3,7-Dimethyl-2-oxo-6-octene-1,3-diol: an aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata (Say)

  摘要：

  (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.

  DOI：

  10.1016/s0040-4039(02)00349-0

文献信息

• 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
  作者：Takuya Tashiro、Kenji Mori

  DOI：10.1016/j.tetasy.2005.03.030

  日期：2005.5

  (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.
• Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer
  作者：Shuo-Ning Li、Ling-Lan Fang、Jiang-Chun Zhong、Jun-Jian Shen、Hao Xu、Yan-Qing Yang、Shi-Cong Hou、Qing-hua Bian

  DOI：10.1016/j.tetasy.2013.12.018

  日期：2014.4

  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.
• Enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol: a Colorado potato beetle pheromone
  作者：Bathini Nagendra Babu、Kamlesh R. Chauhan

  DOI：10.1016/j.tetlet.2008.10.092

  日期：2009.1

  The recent identification of a male-produced aggregation pheromone [(S)-3,7-dimethyl-2-oxo-6-octene1,3-diol, (S)-CPB] offers a new tool for Colorado potato beetle (CPB) management. We developed a novel synthetic approach to produce CPB pheromone in seven steps and 46.54% overall yield. Grignard reaction, oxidation, and stereoselective methylation using organometallic reagent are the key steps in the commercially viable total synthesis, generating CPB pheromone in 98.6% enantiomeric purity and gram quantity. Published by Elsevier Ltd.
• (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.
• Synthesis of the aggregation pheromone of the Colorado potato beetle from its degradation product
  作者：Weronika Wacławczyk-Biedroń、Bożena Frąckowiak-Wojtasek、Daniel Strub、Magdalena Rzechak、Hubert Wojtasek

  DOI：10.1016/j.bmcl.2015.06.083

  日期：2015.9

  Incubation of the Colorado potato beetle aggregation pheromone, (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one, with antennal or leg extracts from this beetle gave 6-methyl-5-hepten-2-one as the major product. This ketone was used as a substrate in a stereoselective synthesis of the pheromone. It was attached to the butanediacetal of glycolic acid with good stereoselectivity and the desired isomer was

  将科罗拉多马铃薯甲虫聚集信息素（S）-1,3-二羟基-3,7-二甲基-6-辛烯-2-酮与该甲虫的触角或腿部提取物一起孵育，得到6-甲基-5-庚烯-二合一为主要产品。该酮用作信息素的立体选择性合成中的底物。将其以良好的立体选择性连接到乙醇酸的丁二缩醛上，并通过在硅胶上纯化该反应的产物来进一步富集所需的异构体。