(2E,10E)-dodeca-2,10-dienedial | 116451-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,10E)-dodeca-2,10-dienedial
• CAS: 116451-85-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: HTFJZARJWDFJSD-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,10E)-dodeca-2,10-dienedial 、 乙炔基溴化镁 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以5.3 mg的产率得到(4E,12E)-hexadeca-4,12-diene-1,15-diyne-3,14-diol
  参考文献：
  名称：

  Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.

  摘要：

  An optically inactive C-20 bisacetylenic alcohol, (4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol, was isolated from a marine sponge Callyspongia sp. as a result of screening of antilymphangiogenic agents from marine invertebrates. An optical resolution using chiral-phase HPLC gave each enantiomer, (-)-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure activity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the "1-yn-3-ol" on both termini and that there is a minimum chain length that connects the "1-yn-3-ol" moieties.

  DOI：

  10.1021/np400297p
• 作为产物：
  描述：

  2,2'-[Dodeca-2,10-diyne-1,12-diylbis(oxy)]bis(oxane) 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 51.0h， 生成 (2E,10E)-dodeca-2,10-dienedial
  参考文献：
  名称：

  Iriye, Ryozo; Toya, Tsutomu; Makino, Junji, Agricultural and Biological Chemistry, 1988, vol. 52, # 4, p. 989 - 996

  摘要：

  DOI：

文献信息

• Bidirectional, Organocatalytic Synthesis of Lepidopteran Sex Pheromones
  作者：Renata Marcia de Figueiredo、Raphael Berner、Jennifer Julis、Ting Liu、David Türp、Mathias Christmann

  DOI：10.1021/jo0620415

  日期：2007.1.1

  Shuffling of two simple building blocks and a regioselective transfer hydrogenation allow for the rapid synthesis of a small collection of lepidopteran sex pheromones, e.g., 8E,10Z-tetradeca-8,10-dienal 5c, from the horse chestnut leafminer (Cameraria ohridella).
• IRIYE, RYOZO;TOYA, TSUTOMU;MAKINO, JUNJI;ARUGA, RYUICHI;DOI, YUKIO;HANDA,+, AGR. AND BIOL. CHEM., 52,(1988) N 4, C. 989-996
  作者：IRIYE, RYOZO、TOYA, TSUTOMU、MAKINO, JUNJI、ARUGA, RYUICHI、DOI, YUKIO、HANDA,+

  DOI：——

  日期：——
• Iriye, Ryozo; Toya, Tsutomu; Makino, Junji, Agricultural and Biological Chemistry, 1988, vol. 52, # 4, p. 989 - 996
  作者：Iriye, Ryozo、Toya, Tsutomu、Makino, Junji、Aruga, Ryuichi、Doi, Yukio、et al.

  DOI：——

  日期：——
• Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge <i>Callyspongia</i> sp.
  作者：Takayuki Shirouzu、Kousuke Watari、Mayumi Ono、Keiichi Koizumi、Ikuo Saiki、Chiaki Tanaka、Rob W. M. van Soest、Tomofumi Miyamoto

  DOI：10.1021/np400297p

  日期：2013.7.26

  An optically inactive C-20 bisacetylenic alcohol, (4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol, was isolated from a marine sponge Callyspongia sp. as a result of screening of antilymphangiogenic agents from marine invertebrates. An optical resolution using chiral-phase HPLC gave each enantiomer, (-)-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure activity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the "1-yn-3-ol" on both termini and that there is a minimum chain length that connects the "1-yn-3-ol" moieties.