2-methyl-4-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecen-18-yl)but-3-yn-2-ol | 218964-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-4-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecen-18-yl)but-3-yn-2-ol
• 英文别名: 4-(2,5,8,11,14,17-Hexaoxabicyclo[16.4.0]docosa-1(18),19,21-trien-20-yl)-2-methylbut-3-yn-2-ol
• CAS: 218964-86-4
• 化学式: C₂₁H₃₀O₇
• 分子量: 394.465
• InChiKey: MWFYZTIQNJXJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecen-18-yl)but-3-yn-2-ol 在 氢氧化钾 作用下， 以 苯 为溶剂， 以69%的产率得到4'-ethynylbenzo-18-crown-6
  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
• 作为产物：
  描述：

  18-iodo-2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecene 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以69%的产率得到2-methyl-4-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecen-18-yl)but-3-yn-2-ol
  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

• ——
  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.