16-(2-hydroxyethyl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane | 81331-61-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 16-(2-hydroxyethyl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
• 英文别名: 2-(1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl)ethanol；N-hydroxyethyl monoaza-18-crown-6；N-(2-hydroxyethyl)-4-aza-18-crown-6；N-(2-hydroxyethyl)-16-aza-18-crown-6；N-(2-hydroxyethyl)aza-18-crown-6；2-(1,4,7,10,13-Pentaoxa-16-azacyclooctadecan-16-yl)ethanol
• CAS: 81331-61-5
• 化学式: C₁₄H₂₉NO₆
• mdl: MFCD00418369
• 分子量: 307.387
• InChiKey: WQJKJSUEVSEYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  16-(2-hydroxyethyl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 在 氯化亚砜 作用下， 反应 1.0h， 生成 16-(2-Chloro-ethyl)-1,4,7,10,13-pentaoxa-16-aza-cyclooctadecane
  参考文献：
  名称：

  Nicotinic acid lariat ethers: syntheses, complexation, and reduction

  摘要：

  DOI：

  10.1021/jo00222a011
• 作为产物：
  描述：

  双[2-(2-氯化乙氧基)乙基]醚 在 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 46.0h， 生成 16-(2-hydroxyethyl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
  参考文献：
  名称：

  从 N,N-二[低聚(氧化烯)]胺和低聚乙二醇二(对甲苯磺酸盐)或相应的二氯化物合成单氮杂冠醚

  摘要：

  通过二乙醇胺或 N,N-二[低聚(氧乙烯)]胺与低聚乙二醇二(对甲苯磺酸盐)或相应的二氯化物在叔丁醇/二恶烷中的一步反应制备了单氮杂冠醚，收率令人满意。存在叔丁醇钠或钾。研究了制备单氮杂15-和18-冠醚的反应条件。还制备了各种具有取代基的单氮杂冠醚并研究了它们的性质。

  DOI：

  10.1246/bcsj.56.212

文献信息

• Synthesis of new fluorophores derived from monoazacrown ethers and coumarin nucleus
  作者：Ernesto Brunet、Pablo García-Losada、Juan-Carlos Rodríguez-Ubis、Olga Juanes

  DOI：10.1139/v02-006

  日期：2002.2.1

  New ionophores derived from azacrown ethers attached to coumarins have been synthesized and characterized. The alkaline-earth complexes of these new ligands were studied from their UV–vis, NMR, and fluorescence data. Some systems displayed bathochromic shifts and fluorescence decreases upon complexation with Ca²⁺ that may make them useful signaling devices of this metal.Key words: alkaline earth, emission, molecular modeling.

  从连接到香豆素的氮杯冠醚衍生的新离子载体已被合成和表征。这些新配体的碱土金属配合物已从它们的紫外-可见、核磁共振和荧光数据中研究。一些系统在与Ca2+形成络合物时显示出巴托克蓝移和荧光减少，这可能使它们成为这种金属的有用信号装置。关键词：碱土金属、发射、分子建模。
• Aza-crown ether locked on polyethyleneimine: solving the contradiction between transfection efficiency and safety during <i>in vivo</i> gene delivery
  作者：Shengran Li、Lin Lin、Wenliang Wang、Xinxin Yan、Binggang Chen、Sangni Jiang、Sanrong Liu、Xiaojing Ma、Huayu Tian、Xifei Yu

  DOI：10.1039/c9cc10041e

  日期：——

  An aza-crown ether derivative to lock a hyperbranched PEI, which endows the PEI with tumor targeting ability, antiserum ability and extended circulation in the blood, meanwhile retaining the high gene complexation and high transfection efficiency.

  一种aza-冠醚衍生物，用于锁定超支化PEI，赋予PEI肿瘤靶向能力、抗血清能力和延长在血液中的循环时间，同时保留高基因结合和高转染效率。
• Complexation and fluorescence behavior of a copolymer bearing azacrown ether and anthracene moieties
  作者：Hidefumi Sakamoto、Tomohiro Anase、Hideji Osuga、Keiichi Kimura

  DOI：10.1016/j.reactfunctpolym.2011.02.003

  日期：2011.5

  K + and K + , respectively. The largest change in fluorescence behavior was observed for the copolymer bearing aza-18-crown-6 in the presence of K + . The magnitude of the increase in the fluorescence intensity was related to the content of the crown ether moiety. The time-dependent changes in the fluorescence spectra using photo-irradiation were also investigated.

  摘要用N -2-乙基氮杂正丁醚或9-羟甲基蒽的甲基丙烯酸酯合成了具有氮杂冠醚和蒽部分的共聚物。在THF：H 2 O = 10：1溶液中测量了它们在碱金属离子存在下的荧光行为。观察到分别带有Na +，K +和K +的带有aza-12-crown-4、15-crown-5和18-crown-6的共聚物的最大荧光强度。在K +存在下，对于带有aza-18-crown-6的共聚物，观察到最大的荧光行为变化。荧光强度增加的幅度与冠醚部分的含量有关。还研究了光辐照下荧光光谱随时间的变化。
• Complexing ability of N-oligoethylene glycol monoaza crown ethers with sodium and potassium cations
  作者：Araki Masuyama、Yohji Nakatsuji、Isao Ikeda、Mitsuo Okahara

  DOI：10.1016/s0040-4039(01)83008-2

  日期：1981.1

  N-Oligoethylene glycol monoaza crown ethers were prepared, and the notable effect of oxyethylene oxygen atoms of the side chain on complexing ability with sodium and potassium cations was confirmed.

  制备了N-低聚乙二醇单氮杂冠醚，证实了侧链的氧亚乙基氧原子对与钠和钾阳离子的络合能力有显着影响。
• Synthesis of azacrown ethers modified with side-chains containing germanium
  作者：Ryoko Suzuki、Takashi Matsumoto、Katsumi Tanaka、Yoshito Takeuchi、Tamotsu Taketomi

  DOI：10.1016/s0022-328x(01)01054-3

  日期：2001.11

  The reaction between ethanolamine (4) and tri- or tetraethylene tosylate (5) and (13) gave 9- and 12-membered monoazacrowns with a -CH2CH2OH residue on nitrogen, A-OH and B-OH, together with 18- and 24-membered diazacrown ethers with the same substituent on nitrogen, E-OH and F-OH. If 2-(2-aminoethoxy)ethanol (12) was used in the reaction described above, instead of 4, the final products, G-OH and H-OH, and K-OH and L-OH, have a longer side chain, -CH2CH2OCH2CH2OH, on nitrogen (Route 1). A series of reactions involving bromoethanol (6) and diethanolamine (9) formed, with 5 or 13, 18- and 24-membered monoazacrowns with the shorter substituent as described above, a 15-membered monoazacrown ether C-OH and an 18-membered D-OH. If 2-(2-chloroethoxy)ethanol (14) is used instead of 6, I-OH and J-OH are obtained (Route 2'). All these hydroxy azacrown ethers were made to react with 3-trimethylgermylpropionic acid (18) to give the corresponding germanium-containing A-L. A preliminary investigation was carried out on the cation transport capability of these germanium-containing azacrown ethers to observe whether germanium might enhance their cation transporting capability. (C) 2001 Published by Elsevier Science B.V.