N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide | 72358-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide
• 英文别名: N,N-bis<2-(2-hydroxyethoxy)ethyl>-4-methylbenzenesulfonamide；N,N-bis[2-(2-hydroxyethoxy)ethyl]-p-toluenesulfonamide；N,N-bis(2-(2-hydroxyethoxy)-ethyl)-4-methylbenzenesulfonamide；N,N-Bis[2-(2-hydroxyethoxy)ethyl]-4-methylbenzene-1-sulfonamide；N,N-bis[2-(2-hydroxyethoxy)ethyl]-4-methylbenzenesulfonamide
• CAS: 72358-83-9
• 化学式: C₁₅H₂₅NO₆S
• 分子量: 347.433
• InChiKey: CGHBCRFYBHRQHA-UHFFFAOYSA-N

物化性质

• 沸点：
  530.1±60.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 222.0h， 生成 4,4'-(2-benzyl-1,3-propanediyl)bis(1,7-dioxa-4,10-diazacyclododecane)
  参考文献：
  名称：

  Lipophilic cage ligands containing two tightly connected 1,7-dioxa-4,10-diazacyclododecane rings: synthesis and x-ray structure of a sodium perchlorate complex

  摘要：

  DOI：

  10.1021/jo00257a016
• 作为产物：
  描述：

  4-methyl-N,N-bis(2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethyl)benzenesulfonamide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 N,N-bis<2-(2-hydroxyethoxy)ethyl>-p-toluenesulfonamide
  参考文献：
  名称：

  阳离子络合双N，N '桥联的双-（1,7-二氧杂-4,10-二氮杂环十二烷）的合成

  摘要：

  可以在两个受控步骤中通过氮原子之间的两个乙烯桥将两个diaza-12-crown-4分子连接，其中最后一个需要以Li阳离子为模板，尽管Na阳离子与三环穴状类似物的结合最强。

  DOI：

  10.1039/c39810001084

文献信息

• Design and synthesis of macrocyclic ligands for specific interaction with crystalline ettringite and demonstration of a viable mechanism for the setting of cement
  作者：Jonathan L. W. Griffin、Peter V. Coveney、Andrew Whiting、Roger Davey

  DOI：10.1039/a902760b

  日期：——

  Cementitious materials are among those most widely used by mankind while being among the least well understood. The detailed physicochemical processes involved in the hydration and setting of cement slurries are very complex, and a clearly defined quantitative account is still lacking; indeed, even the composition of the cement powder itself is not known exactly. Still less has there been any understanding of the mechanism by which numerous known retarders of the cement setting process act. In this article, we detail the synthesis of novel macrocyclic organophosphonate retarders 1a and 2a which were developed by rational methods. Attempts to synthesise these compounds as phosphonate ester derivatives were universally unsuccessful, however direct modification of the parent hexaaza- (3) and trioxatriaza-18-crown-6 (5) derivatives was successful, to provide the phosphonic acids 1b and 2b respectively. Subsequent testing of these compounds showed their ability to inhibit the growth of crystalline ettringite and delay the setting of cement. These results support the hypothesis that the formation of crystalline ettringite is the rate determining step in the setting of cement.

  水硬性材料是人类使用最广泛却最不为人所了解的材料之一。水泥浆体的水化和凝结涉及的详细的物理化学过程非常复杂，目前仍缺乏明确的定量解释；事实上，甚至连水泥粉体的成分也无法确切知晓。更不用说，对于已知的大量抑制水泥凝结过程的缓凝剂的作用机理也缺乏了解。在本文中，我们详细介绍了新型大环有机膦酸酯缓凝剂1a和2a的合成过程，这些缓凝剂是通过合理方法开发的。然而，尝试将这些化合物合成磷酸酯衍生物均未成功，相反，直接修饰母体六氮杂（3）和三氧三氮杂-18-冠-6（5）衍生物获得了成功，分别得到了膦酸1b和2b。随后对这些化合物的测试表明，它们能够抑制结晶钙矾石的生长并延缓水泥的凝结。这些结果支持了如下假设：结晶钙矾石的形成是水泥凝结速率的决定步骤。
• Diazadibenzo-30-crown-10 derivatives as receptors for diquat
  作者：Pier Lucio Anelli、Neil Spencer、J.Fraser Stoddart

  DOI：10.1016/s0040-4039(00)80354-8

  日期：——

  In acetone-d6 solution, 1H n.m.r. spectroscopy reveals that receptors 4–9, prepared from the readily-synthesised diazadibenzo-30-crown-10 derivative 1, form strong 1:1 molecular inclusion complexes with Diquat, which, although present mainly as the dication, is accompanied by trace amounts of the radical cation.

  在丙酮-d 6溶液，1 H NMR光谱表明，受体4 - 9中，从容易合成的二苯并-30冠10衍生物制备1，形成强1：敌草快1分子包合复合物，其虽然目前主要作为该指示伴随着痕量的自由基阳离子。
• Boerjesson, L.; Welch, C. J., Acta Chemica Scandinavica, 1991, vol. 45, # 6, p. 621 - 626
  作者：Boerjesson, L.、Welch, C. J.

  DOI：——

  日期：——
• Synthesis and complexation properties of suitcase-shaped macrotricyclic and butterfly-shaped macrobicyclic polyether ligands
  作者：Haoyun An、Jerald S. Bradshaw、Krzysztof E. Krakowiak、Chengyue Zhu、N. Kent Dalley、Reed M. Izatt

  DOI：10.1021/jo00044a040

  日期：1992.8

  Ten suitcase-shaped macrotricyclic polyethers (1-10) containing nitrogen and carbon bridgehead atoms have been synthesized. These new cage compounds were prepared by connecting together two hydroxymethyl-substituted or two secondary amine-containing butterfly-shaped macrobicyclic polyethers by means of linear bifunctional connecting groups. Intermediate bis(hydroxymethyl)-substituted butterfly-shaped macrobicyclic polyether 14 was prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 5-methylene-3,7-dioxanonane-1,9-diyl ditosylate to give bislariat 1,4-diaza-13-crown-4 (11) which was cyclized with 3-chloro-2-(chloromethyl)-l-propene followed by hydroboration. Intermediate bissecondary amine-contaminating butterfly shaped macrobicyclic polyethers 18 and 19 were prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 6-tosyl-3,9-dioxa-6-aza-1,11-undecanediyl ditosylate (33) to give N-tosyl-N,N"-bis(2-hydroxyethyl)triaza-15-crown-5 (12). Lariat crown ether 12 was cyclized with 33 followed by reduction with LiAlH4 to give 18, or with 4-tosyl-4-aza-1,7-heptanediyl ditosylate (36) to give 19. Some of the suitcase-shaped macrotricycles interacted with various cations. One was selective for Pb2+ ions and another interacted strongly with Hg2+. A crystal structure for the 13-NaClO4 complex also is reported.
• Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines
  作者：Erik F. J. de Vries、Pablo Steenwinkel、Johannes Brussee、Chris G. Kruse、Arne van der Gen

  DOI：10.1021/jo00068a029

  日期：1993.7

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.