(2E,6Z)-3-ethyl-7-methyl-2,6-nonadien-1-ol | 32775-49-8

• 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,6Z)-3-ethyl-7-methyl-2,6-nonadien-1-ol
• 英文别名: (2E,6Z)-3-ethyl-7-methyl-nona-2,6-dien-1-ol；3-Ethyl-7-methyl-nonadien-(2trans,6cis)-ol-(1)；3-Aethyl-7-methyl-nonadien-(2trans,6cis)-ol；Bishomogeraniol；(2E,6Z)-3-ethyl-7-methylnona-2,6-dien-1-ol
• CAS: 32775-49-8
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: ULDAYFCHOKIWBN-VNPQWULESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,6Z)-3-ethyl-7-methyl-2,6-nonadien-1-ol 在 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 dihomogeranyl diphosphate
  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：

  (Z)-7-methyl-non-6-en-2-yn-1-ol 生成 (2E,6Z)-3-ethyl-7-methyl-2,6-nonadien-1-ol
  参考文献：
  名称：

  Stereospecific total synthesis of the dl-C18 Cecropia juvenile hormone

  摘要：

  DOI：

  10.1021/ja01022a060

文献信息

• THE STEREOSPECIFIC PREPARATION OF METHYL FARNESOATE AND SYNTHETIC PRECURSORS OF C₁₈- AND C₁₇JUVENILE HORMONES
  作者：Susumu Kobayashi、Teruaki Mukaiyama

  DOI：10.1246/cl.1974.1425

  日期：1974.12.5

  The new method for the stereospecific preparation of 1,5-diene units was successfully applied to the syntheses of methyl farnesoate and the synthetic precursors of C18- and C17 juvenile hormones, 15 and 20.

  这种新方法成功地用于立体特异性制备1,5-二烯单元，应用于合成甲基法尼酸酯以及C18和C17幼虫激素的合成前体15和20。
• Stereospecific synthesis of a biologically active dehydro derivative of the C18-juvenile hormone of cecropia. New routes to a key C12-intermediate
  作者：E.J. Corey、John A. Katzenellenbogen、Steven A. Roman、Norman W. Gilman

  DOI：10.1016/s0040-4039(01)87471-2

  日期：1971.1
• US4006193A
  申请人：——

  公开号：US4006193A

  公开（公告）日：1977-02-01