4'-ethynylbenzo-18-crown-6 | 92710-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-ethynylbenzo-18-crown-6
• 英文别名: 18-Ethynyl-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]hexaoxacyclooctadecine；20-ethynyl-2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-triene
• CAS: 92710-95-7
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: STBDGSYRBRVAQC-UHFFFAOYSA-N

物化性质

• 沸点：
  482.4±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4'-ethynylbenzo-18-crown-6 在 吗啉 、 聚合甲醛 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到1,4-bis(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-hexaoxabenzocyclooctadecen-18-yl)buta-1,3-diyne
  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 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 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

文献信息

• Synthesis of light-harvesting dendrimers focally anchored with crown ethers or terpyridine ligands
  作者：Yongchun Pan、Meng Lu、Zhonghua Peng、Joseph S. Melinger

  DOI：10.1039/b307507a

  日期：——

  extenction coefficients and high fluoresence quantum yields. Coordination of crown ethers with alkali ions results in a significant increase in absorption strength in the UV range, but little alteration in either intensity or position of fluorescence emission. Coordination of terpyridine ligands with Ru2+, however, does efficiently quench the fluorescence from the dendrons,albeit only the smallest dendron

  冠醚和吡啶吡啶配体已通过Pd催化的偶联反应成功连接到光收集苯乙炔单树枝状化合物的焦点上。这些功能性单树枝的结构通过1H和13C NMR光谱，质谱和元素分析进行​​了表征。这种结合配体锚定的树枝状分子显示出宽的吸收，大的摩尔延伸系数和高的荧光量子产率。冠醚与碱离子的配位会导致UV范围内的吸收强度显着提高，但荧光发射的强度或位置几乎没有变化。联吡啶配体与Ru2 +的配位可有效地猝灭树枝状分子的荧光，尽管只有最小的树枝状分子显示出有效的结合。
• Nematic liquid crystal compounds containing a benzocrown ether unit
  作者：Gong-Xin He、Fumio Wada、Kiyoshi Kikukawa、Tsutomu Matsuda

  DOI：10.1039/c39870001294

  日期：——

  Benzocrown ethers carrying a para-substituted biphenyl group, (1a–c and 2a,b), display a nematic liquid crystal phase; selective complexation with picrates in the liquid crystal phase was observed by doping experiments.

  带有对位取代联苯基（1a – c和2a，b）的苯并冠醚显示出向列型液晶相。通过掺杂实验观察到在液晶相中与苦味酸盐的选择性络合。
• Reconfiguration of the Symmetry and Charge-Transfer Characteristics of a Triply Crowned 1,3,5-Tris(arylalkynyl)mesitylene by Successive Metal Ion Complexation
  作者：Gunther Hennrich、Knut Rurack、Monika Spieles

  DOI：10.1002/ejoc.200500595

  日期：2006.1

  A triply benzocrown-ether-functionalized trialkynylmesitylene derivative with C3 symmetry as well as its linear analogue have been synthesized and their optical properties have been studied by UV/Vis absorption, steady-state and time-resolved fluorescencece spectroscopy. The spectroscopic investigation of the uncomplexed compounds revealed the nature of the electronic and excitonic communication pathway

  合成了具有 C3 对称性的三重苯并冠醚官能化三炔基均三甲苯衍生物及其线性类似物，并通过紫外/可见吸收、稳态和时间分辨荧光光谱研究了它们的光学性质。未复合化合物的光谱研究揭示了全间位取代发色团系统的基态和激发态中电子和激子通信途径的性质。阳离子络合后，游离三炔基化合物的八极特性变为偶极，最终在完全络合的物质中恢复为八极。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Syntheses and thermal properties of new liquid crystals bearing a crown ether ring: cation binding in the nematic phase
  作者：Gong Xin He、Fumio Wada、Kiyoshi Kikukawa、Seiji Shinkai、Tsutomu Matsuda

  DOI：10.1021/jo00289a028

  日期：1990.1
• FLUORESCENCE COMPOUND, ION CONCENTRATION SENSOR INCLUDING THE COMPOUND, REAGENT INCLUDING COMPOUND, REAGENT KIT PROVIDED WITH REAGENT, AND METHOD FOR SYNTHESIZING COMPOUND
  申请人：National University Corporation Hokkaido University

  公开号：EP2684881B1

  公开（公告）日：2018-11-28