(2E,6E,10Z)-3,7,11-trimethyl-2,6,10-tridecatrien-1-ol | 30310-67-9

• 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,10Z)-3,7,11-trimethyl-2,6,10-tridecatrien-1-ol
• 英文别名: Homofarnesol；12-Homofarnesol；(2E,6E,10Z)-3,7,11-trimethyl-trideca-2,6,10-trien-1-ol；(2E,6E,10Z)-3,7,11-trimethyltrideca-2,6,10-trien-1-ol
• CAS: 30310-67-9
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: IHNFFXKWKNXCRZ-YLIIGXAQSA-N

物化性质

• 沸点：
  334.3±11.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-6-((tert-butyldiphenylsilyl)oxy-4methylhex-4-enal) 在 Wilkinson's catalyst manganese(IV) oxide 、 18-冠醚-6 、 联苯 、 barium(II) iodide 、 四丁基氟化铵 、 氢气 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 12.25h， 生成 (2E,6E,10Z)-3,7,11-trimethyl-2,6,10-tridecatrien-1-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

• Syntheses of Cecropia Juvenile Hormones by Selective Side-chain Methylation of (<i>E</i>,<i>E</i>)-Farnesol
  作者：Arata Yasuda、Shin Tanaka、Hisashi Yamamoto、Hitosi Nozaki

  DOI：10.1246/bcsj.52.1701

  日期：1979.6

  The stereoselective route to the title insect hormones (JH-1 & JH-2) depends crucially on the epoxidation of allylic alcohols with t-butyl hydroperoxide in the presence of oxobis(2,4-pentanedionato-O,O′)vanadium(IV). The oxidation of 2-methyl-1-hepten-3-ol exclusively produces the (2R*,3S*) isomerofthe diastereomeric epoxy alcohols. This is converted into (Z)-6-methyl-5-undecene by the sequence involving oxirane reaction with lithium dibutylcuprate(I) and the removal of both hydroxyl groups of the resulting 1,2-diol. Extension of the series of reactions to the mono- and bisoxirane derived from (E,E)-farnesol gives JH-2 and JH-1, respectively.

  获得上述昆虫激素（JH-1 和 JH-2）的立体选择性途径主要取决于烯丙基醇在氧代双（2,4-戊二酮酸-O,O′）钒（IV）存在下与叔丁基过氧化氢发生的环氧化反应。2- 甲基-1-庚烯-3-醇的氧化反应只产生非对映异构环氧醇的 (2R*,3S*)异构体。通过与二丁基杯酸锂（I）发生环氧乙烷反应，并去除所生成的 1,2-二醇的两个羟基，从而将其转化为 (Z)-6-甲基-5-十一烯。将这一系列反应扩展到从(E,E)-法呢醇得到的单环氧乙烷和双环氧乙烷，可分别得到 JH-2 和 JH-1。
• Synthesis of compounds with juvenile hormone activity—XVII
  作者：K. Mori、M. Ohki、M. Matsui

  DOI：10.1016/s0040-4020(01)97156-x

  日期：1974.1
• 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.