1,5,9,13-tetradecatetraene | 51487-38-8

• 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-tetradecatetraene
• 英文别名: tetradeca-1,5,9,13-tetraene
• CAS: 51487-38-8
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: DHLQCLRZNQGXIE-UHFFFAOYSA-N

物化性质

• 沸点：
  250.1±30.0 °C(Predicted)
• 密度：
  0.802±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。

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

安全信息

• 海关编码：
  2901299090

反应信息

• 作为反应物：
  描述：

  1,5,9,13-tetradecatetraene 在 potassium osmate(VI) 、 Hydroquinone 1,4-phthalazinediyl diether 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18%的产率得到(5S,6S,9S,10S)-tetradeca-1,12-diene-5,6,9,10-tetraol
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  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.

  DOI：

  10.1021/ja0660148

文献信息

• Elucidation of double‐bond positions of polyunsaturated alkenes through gas chromatography/mass spectrometry analysis of mono‐dimethyl disulfide derivatives
  作者：Sian Liao、Gordon Sherman、Yongsong Huang

  DOI：10.1002/rcm.9228

  日期：2022.1.30

  dimethyl disulfide (DMDS) followed by gas chromatography/mass spectrometry (GC/MS) analysis is a well-established method for locating double-bond position on the alkyl chain of mono-unsaturated compounds such as alkenes. For alkenes containing more than one double bond, however, the conventional DMDS derivatization approach forms poly- or cyclized DMDS adducts whose mass spectra are difficult to interpret

  用二甲基二硫化物 (DMDS) 衍生化，然后进行气相色谱/质谱 (GC/MS) 分析是一种成熟的方法，用于定位烯烃等单不饱和化合物的烷基链上的双键位置。然而，对于含有一个以上双键的烯烃，传统的 DMDS 衍生方法会形成多聚或环化 DMDS 加合物，其质谱很难根据双键位置来解释。在这项研究中，我们报告了一种有效的实验程序来生产具有 2 到 6 个双键的多不饱和烯烃的单 DMDS 加合物。这些单 DMDS 加合物的 GC / MS 分析产生了高度特征性的质量碎片，允许明确分配烷基链上的双键位置。我们还应用了我们的新方法（即，Isochrysis litoralis，一种触体藻类。
• 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.
• 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.