(R)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one | 443361-62-4

• 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-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
• CAS: 443361-62-4
• 化学式: C₂₆H₃₆O₃Si
• 分子量: 424.656
• InChiKey: SNZCJXNPAQMSBA-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one 在 四丁基氟化铵 作用下， 生成 (R)-1,3-dihydroxy-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
• 作为产物：
  描述：

  (2S,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 以83%的产率得到(R)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one
  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

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.