homogeranyl pyrophosphate | 73876-52-5

• 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: homogeranyl pyrophosphate
• 英文别名: (2E,6Z)-3,7-dimethyl-2,6-nonadien-1-yl diphosphate；[(2E,6Z)-3,7-dimethylnona-2,6-dienyl] phosphono hydrogen phosphate
• CAS: 73876-52-5
• 化学式: C₁₁H₂₂O₇P₂
• 分子量: 328.239
• InChiKey: BWPDNDNFSUZDKQ-YANFREPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  homogeranyl pyrophosphate 在 三乙基硅烷 、 manganese(IV) oxide 、 Tris-HCl buffer 、 DL-dithiothreitol 、 geranylgeranial 、 (Ph₃P)3PhCl 、 farnesyl pyrophosphate synthetase 、 hydrolising reagent 、 2-巯基乙醇 、 alkaline phosphatase 作用下， 反应 0.5h， 生成 3(S),4(S)-faranal
  参考文献：
  名称：

  Bioorganic synthesis and absolute configuration of faranal

  摘要：

  DOI：

  10.1021/ja00541a057
• 作为产物：
  描述：

  (E)-6-((tert-butyldiphenylsilyl)oxy-4methylhex-4-enal) 在 N-氯代丁二酰亚胺 、 18-冠醚-6 、 2,3-二巯基丁二酸 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 homogeranyl pyrophosphate
  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.
• Bioorganic synthesis and absolute configuration of faranal
  作者：Masaki Kobayashi、Tanetoshi Koyama、Kyozo Ogura、Shuichi Seto、F. J. Ritter、I. E. M. Brueggemann-Rotgans

  DOI：10.1021/ja00541a057

  日期：1980.10