(2E,6E)-1-[tert-butyl(diphenyl)silyl]oxy-3,7,11-trimethyldodeca-2,6,10-trien-4-ol | 189438-06-0

• 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: (2E,6E)-1-[tert-butyl(diphenyl)silyl]oxy-3,7,11-trimethyldodeca-2,6,10-trien-4-ol
• CAS: 189438-06-0
• 化学式: C₃₁H₄₄O₂Si
• 分子量: 476.775
• InChiKey: VBMJBZBMDCQZLP-YAMZXTECSA-N

物化性质

• 沸点：
  542.2±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,6E)-1-[tert-butyl(diphenyl)silyl]oxy-3,7,11-trimethyldodeca-2,6,10-trien-4-ol 在 三溴化磷 作用下， 生成 [(2E,6E)-4-bromo-3,7,11-trimethyldodeca-2,6,10-trienoxy]-tert-butyl-diphenylsilane 、 [(3E,6E)-2-bromo-3,7,11-trimethyldodeca-3,6,10-trienoxy]-tert-butyl-diphenylsilane
  参考文献：
  名称：

  Natural and Unnatural Terpenoid Precursors of Insect Juvenile Hormone

  摘要：

  The biosynthesis of insect juvenile hormone (JH) is due, in part, to the precise head-to-tail coupling of allylic and homoallylic diphosphate substrates, as catalyzed by one or more prenyltransferases. To better understand this enzyme's role in JH production, homodimethylallyl diphosphate and both the natural and unnatural homologs of geranyl diphosphate have been prepared as potential substrates for insect prenyltransferase. These latter materials were constructed in a convergent manner by olefination of the corresponding trisnoraldehydes obtained from either terminal oxidative cleavage of geraniol or higher-order cuprate conjugate addition to acrolein. To aid in characterizing the nature of the terpenoid skeletons formed from our in vitro studies, homologous derivatives of farnesol were also prepared by anion coupling of the geranyl derivatives to either C-5 or C-6 allylic bromides. The preparation of these materials and the results of incubations with larval corpora allata homogenates of the lepidopteran Manduca sexta are described.

  DOI：

  10.1021/jo962008q
• 作为产物：
  描述：

  tert-butyl(3-methylbut-2-enyloxy)diphenylsilane 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 联苯 、 barium(II) iodide 、 水 、 水杨酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.25h， 生成 (2E,6E)-1-[tert-butyl(diphenyl)silyl]oxy-3,7,11-trimethyldodeca-2,6,10-trien-4-ol
  参考文献：
  名称：

  Natural and Unnatural Terpenoid Precursors of Insect Juvenile Hormone

  摘要：

  The biosynthesis of insect juvenile hormone (JH) is due, in part, to the precise head-to-tail coupling of allylic and homoallylic diphosphate substrates, as catalyzed by one or more prenyltransferases. To better understand this enzyme's role in JH production, homodimethylallyl diphosphate and both the natural and unnatural homologs of geranyl diphosphate have been prepared as potential substrates for insect prenyltransferase. These latter materials were constructed in a convergent manner by olefination of the corresponding trisnoraldehydes obtained from either terminal oxidative cleavage of geraniol or higher-order cuprate conjugate addition to acrolein. To aid in characterizing the nature of the terpenoid skeletons formed from our in vitro studies, homologous derivatives of farnesol were also prepared by anion coupling of the geranyl derivatives to either C-5 or C-6 allylic bromides. The preparation of these materials and the results of incubations with larval corpora allata homogenates of the lepidopteran Manduca sexta are described.

  DOI：

  10.1021/jo962008q

文献信息

• Natural and Unnatural Terpenoid Precursors of Insect Juvenile Hormone
  作者：Stephanie E. Sen、Gregory J. Ewing

  DOI：10.1021/jo962008q

  日期：1997.5.1

  The biosynthesis of insect juvenile hormone (JH) is due, in part, to the precise head-to-tail coupling of allylic and homoallylic diphosphate substrates, as catalyzed by one or more prenyltransferases. To better understand this enzyme's role in JH production, homodimethylallyl diphosphate and both the natural and unnatural homologs of geranyl diphosphate have been prepared as potential substrates for insect prenyltransferase. These latter materials were constructed in a convergent manner by olefination of the corresponding trisnoraldehydes obtained from either terminal oxidative cleavage of geraniol or higher-order cuprate conjugate addition to acrolein. To aid in characterizing the nature of the terpenoid skeletons formed from our in vitro studies, homologous derivatives of farnesol were also prepared by anion coupling of the geranyl derivatives to either C-5 or C-6 allylic bromides. The preparation of these materials and the results of incubations with larval corpora allata homogenates of the lepidopteran Manduca sexta are described.