1,5,9,13-Tetradecatetraen | 62029-44-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,5,9,13-Tetradecatetraen
• 英文别名: (E,E)-1,5,9,13-tetradecatetraene；1,5,9,13-Tetradecatetraene；(5E,9E)-tetradeca-1,5,9,13-tetraene
• CAS: 62029-44-1
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: DHLQCLRZNQGXIE-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,5,9,13-Tetradecatetraen 在 Hydroquinone 1,4-phthalazinediyl diether 、 potassium osmate dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以19%的产率得到(5S,6S,9S,10S)-tetradeca-1,12-diene-5,6,9,10-tetraol
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959
• 作为产物：
  描述：

  (4E,8E)-dodeca-4,8-dienedial 、 甲基三苯基溴化膦 在 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 以79%的产率得到1,5,9,13-Tetradecatetraen
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959

文献信息

• Total Synthesis of (+)-<i>cis</i>-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium
  作者：Timothy J. Donohoe、Robert M. Harris、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja0660148

  日期：2006.10.1

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.
• KAWAI, TADASHI;YAMAZAKI, YASUO;NISHIKAWA, MASANORI, J. JAP. PETROL. INST., 1984, 27, N 5, 378-384
  作者：KAWAI, TADASHI、YAMAZAKI, YASUO、NISHIKAWA, MASANORI

  DOI：——

  日期：——
• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.