trimethyl-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecen-15-yl)ethynyl]silane | 92710-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trimethyl-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecen-15-yl)ethynyl]silane
• 英文别名: 4'-(2-Trimethylsilyleth-1-ynyl)benzo-15-crown-5；Trimethyl-[2-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)ethynyl]silane
• CAS: 92710-92-4
• 化学式: C₁₉H₂₈O₅Si
• 分子量: 364.514
• InChiKey: RXCNVQXWGKGBSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trimethyl-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecen-15-yl)ethynyl]silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89.5%的产率得到4'-乙炔基苯并15-冠-5
  参考文献：
  名称：

  The synthesis and structural characterization of the first bis(benzocrown ethers) with polyyne linkages †

  摘要：

  成功合成了双(苯并-15-冠醚-5)丁-1,3-二炔和双(苯并-15-冠醚-5)辛-1,3,5,7-四炔，并利用 X 射线晶体学对其进行了表征。此外，还研究了聚[双（苯并冠醚）二乙炔]的实验。

  DOI：

  10.1039/b001856m
• 作为产物：
  描述：

  15-iodo-2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecane 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.5h， 以87%的产率得到trimethyl-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecen-15-yl)ethynyl]silane
  参考文献：
  名称：

  摘要：

  4 ' -Ethynylbenzo-12-crown-4 (8), 4 ' -ethynylbenzo-15-crown-5 (9), and 4 ' -ethynylbenzo-18-crown-6 (10) were synthesized by cross-coupling of the corresponding aryl iodides 1-3 with 2-methylbut-3-yn-2-ol (4a) followed by the retro-Favorsky cleavage of the resulting carbinols. Unlike the corresponding benzo-12-crown-4 derivative (5a), the cleavage of tertiary acetylenic, alcohols of benzo-15-crown-5 (6a) and benzo-18-crown-6 (7a) requires more than one molar equivalent of KOH. Aminoalkylation of crown ether 8 gives Mannich bases, independently of the reaction conditions and the nature of amine. The aminomethylation of acetylenic crown ethers 9 and 10 with paraform-piperidine (morpholine) in the presence of CuCl yields 1,4-disubstituted buta-1,3-diynes (19, 20) rather than Mannich bases.

  DOI：

  10.1023/a:1011367311643

文献信息

• The synthesis and structural characterization of the first bis(benzocrown ethers) with polyyne linkages †
  作者：Liang-Hui Lee、Vincent Lynch、Richard J. Lagow

  DOI：10.1039/b001856m

  日期：——

  Bis(benzo-15-crown-5)buta-1,3-diyne and bis(benzo-15-crown-5)octa-1,3,5,7-tetrayne were successfully synthesized and characterized by X-ray crystallography. Experiments with poly[bis(benzocrown ethers)diacetylene] were also studied.

  成功合成了双(苯并-15-冠醚-5)丁-1,3-二炔和双(苯并-15-冠醚-5)辛-1,3,5,7-四炔，并利用 X 射线晶体学对其进行了表征。此外，还研究了聚[双（苯并冠醚）二乙炔]的实验。
• ——
  作者：S. V. Klyatskaya、E. V. Tretyakov、S. F. Vasilevsky

  DOI：10.1023/a:1011367311643

  日期：——

  4 ' -Ethynylbenzo-12-crown-4 (8), 4 ' -ethynylbenzo-15-crown-5 (9), and 4 ' -ethynylbenzo-18-crown-6 (10) were synthesized by cross-coupling of the corresponding aryl iodides 1-3 with 2-methylbut-3-yn-2-ol (4a) followed by the retro-Favorsky cleavage of the resulting carbinols. Unlike the corresponding benzo-12-crown-4 derivative (5a), the cleavage of tertiary acetylenic, alcohols of benzo-15-crown-5 (6a) and benzo-18-crown-6 (7a) requires more than one molar equivalent of KOH. Aminoalkylation of crown ether 8 gives Mannich bases, independently of the reaction conditions and the nature of amine. The aminomethylation of acetylenic crown ethers 9 and 10 with paraform-piperidine (morpholine) in the presence of CuCl yields 1,4-disubstituted buta-1,3-diynes (19, 20) rather than Mannich bases.