eicosa-7,9,11,13-tetrayne | 130049-16-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: eicosa-7,9,11,13-tetrayne
• 英文别名: 7,9,11,13-eicosatetrayne；icosa-7,9,11,13-tetrayne；7,9,11,13-icosatetrayne
• CAS: 130049-16-0
• 化学式: C₂₀H₂₆
• 分子量: 266.426
• InChiKey: GQRQVXNPKDMOAC-UHFFFAOYSA-N

物化性质

• 沸点：
  376.1±25.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,3-癸二炔 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到eicosa-7,9,11,13-tetrayne
  参考文献：
  名称：

  Balova, I. A.; Remizova, L. A., Russian Journal of Organic Chemistry, 1994, vol. 30, # 2.1, p. 213 - 215

  摘要：

  DOI：

文献信息

• A one-pot synthesis of 1-arylalka-1,3-diynes by sequential acetylene zipper and Sonogashira reactions
  作者：Irina A. Balova、Svetlana N. Morozkina、David W. Knight、Sergei F. Vasilevsky

  DOI：10.1016/s0040-4039(02)02496-6

  日期：2003.1

  1,3-Diynes, formed in situ by base-induced acetylene zipper reactions, following anion quenching with water, undergo smooth Sonogashira-type couplings with functionalized aryl iodides, to give good overall yields of 1-arylalka-1,3-diynes.

  用水淬灭阴离子后，由碱诱导的乙炔拉链反应在原位形成的1,3-二炔，与官能化的芳基碘化物进行平滑的Sonogashira型偶合，得到1-芳烷基-1,3-二炔的良好总收率。
• A Convenient Synthesis of Functionalised 1-Aryl-1,3-alkadiynes
  作者：Irina A. Balova、Victor N. Sorokoumov、Svetlana N. Morozkina、Olga V. Vinogradova、David W. Knight、Sergey F. Vasilevsky

  DOI：10.1002/ejoc.200400688

  日期：2005.3

  A two-step, one-pot synthesis of functionalised 1-arylalka-1,3-diynes is described. A key feature in this approach is exploitation of the “acetylene zipper” reaction to obtain terminal 1,3-alkadiynes 3 from internal isomers 1. Without isolation, but after protonation, the 1,3-alkadiynes 3 are subjected to subsequent Pd/Cu-catalyzed Sonogashira cross-couplings with aryl iodides having both electron-withdrawing

  描述了功能化 1-arylalka-1,3-二炔的两步一锅合成。这种方法的一个关键特征是利用“乙炔拉链”反应从内部异构体 1 中获得末端 1,3-烷二炔 3。无需分离，但在质子化后，1,3-烷二炔 3 受到后续 Pd/Cu -催化 Sonogashira 与具有吸电子和给电子基团的芳基碘化物交叉偶联。整个序列在温和的反应条件下进行，以高产率提供官能化的 1-芳基烷-1,3-二炔 21-35。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis and properties of diacetylene azides
  作者：I. N. Domnin、L. A. Remizova

  DOI：10.1134/s1070428009080028

  日期：2009.8

  A three-stage method was developed for the synthesis of diacetylene azides from diacetylene alcohols prepared by Cadiot-Chodkiewicz reaction. By their bromination the corresponding diacetylene bromides were obtained whose azidation resulted in the target diacetylene azides. The attempt was performed to prepare azides of triacetylene series, but the low stability of the synthesized triacetylene alcohols prevented their conversion into the corresponding bromides.
• Synthesis and Characterization of Cyclic Alkyl Tetraynes
  作者：Andreea Spantulescu、Thanh Luu、Yuming Zhao、Robert McDonald、Rik R. Tykwinski

  DOI：10.1021/ol702898a

  日期：2008.2.1

  Cyclic (4a-e) and linear (10) tetraynes have been studied. Macrocycles 4a-e are unstable to isolation as neat compounds, but 4b-e have been characterized in solution. C-13 NMR spectroscopy shows a consistent downfield shift of the acetylenic resonances of 4c-e as ring strain increases. UV-vis spectroscopy demonstrates that ring strain has little effect on the HOMO-LUMO gap. X-ray crystallography of tetrabromoolefin 6b confirms the monomeric constitution of the precursors.
• “Acetylene Zipper” Reactions and Pd-Cu-Catalyzed Cross-coupling in the Synthesis of Vicinal 1,3-Alkadiynylarylamines and Aminopyridines
  作者：I. A. Balova、S. N. Morozkina、V. N. Sorokoumov、O. V. Vinogradova、S. F. Vasilevskii

  DOI：10.1023/b:rujo.0000013136.99262.26

  日期：2003.11

  A preparative method was developed for vicinal-substituted 1,3-alkadiynylarylamines and aminopyridines involving a successive application of "acetylene zipper" reaction to synthesize 1,3-alkadiynes followed by Sonogashira reaction.