6-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]hexanol | 401601-02-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]hexanol
• 英文别名: Teoc-NH(CH2)6OH；2-(Trimethylsilyl)ethyl (6-hydroxyhexyl)carbamate；2-trimethylsilylethyl N-(6-hydroxyhexyl)carbamate
• CAS: 401601-02-3
• 化学式: C₁₂H₂₇NO₃Si
• 分子量: 261.437
• InChiKey: XRNWAZHHESTMTM-UHFFFAOYSA-N

物化性质

• 沸点：
  364.0±27.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]hexanol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以84 %的产率得到2-(trimethylsilyl)ethyl (6-bromohexyl)carbamate
  参考文献：
  名称：

  LIGANDS FOR CAPTURING MICROVESICLES AND USES THEREOF

  摘要：

  The invention relates to ligands able to bind to microvesicles, comprising a plurality of metal(II)-dipicolylamine moieties and their use in the diagnosis or prognostic of disorders in a subject.

  公开号：

  US20220326228A1
• 作为产物：
  描述：

  6-氨基-1-己醇 、 对硝基苯基三甲基硅乙基碳酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86.7%的产率得到6-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]hexanol
  参考文献：
  名称：

  Dendron功能化核壳超顺磁性纳米粒子：铃木C的磁性可回收和可重复使用的催化剂？C交叉偶联反应

  摘要：

  合成了用二环己基二膦基钯配合物官能化的金属十二烷基。所述metallodendron接枝到核-壳纳米颗粒的超顺磁（γ-的Fe 2 ö 3 /聚合物，200-500纳米）的交叉偶联反应以得到最佳的催化活性。接枝的纳米颗粒用作铃木C的可回收和可重复使用的催化剂C交叉偶联反应。它们在温和的条件下对碘和溴代芳烃显示出显着的反应性，对氯代芳烃具有前所未有的反应性。催化反应完成后，通过使用简单的磁体吸引超顺磁性接枝的纳米颗粒，即可轻松回收催化剂。催化剂被回收超过25次，几乎没有明显的反应性损失。

  DOI：

  10.1002/chem.200901866

文献信息

• Structure–Activity Relationship Studies of Argiotoxins: Selective and Potent Inhibitors of Ionotropic Glutamate Receptors
  作者：Mette H. Poulsen、Simon Lucas、Tinna B. Bach、Anne F. Barslund、Claudius Wenzler、Christel B. Jensen、Anders S. Kristensen、Kristian Strømgaard

  DOI：10.1021/jm301602d

  日期：2013.2.14

  open-channel blocker of ionotropic glutamate (iGlu) receptors. Here, three series of analogues were designed to exploit selectivity among iGlu receptors, taking advantage of a recently developed solid-phase synthetic methodology for the synthesis of ArgTX-636 and analogues. Initially, the importance of secondary amino groups in the polyamine chain was studied by the synthesis of systematically modified

  Argiotoxin-636（ArgTX-636），来自蜘蛛Argiope lobata的天然产物，是离子型谷氨酸（iGlu）受体的有效但非选择性的开放通道阻滞剂。在这里，设计了三个系列的类似物，以利用iGlu受体之间的选择性，利用最近开发的用于合成ArgTX-636和类似物的固相合成方法。最初，通过合成系统修饰的ArgTX-636类似物研究了多胺链中仲氨基的重要性，并对其在NMDA和AMPA受体上的药理活性进行了评估。这导致鉴定出分别优先于NMDA和AMPA受体的两种化合物。通过系统地改变芳族头基和连接基氨基酸，可以进一步修饰这些化合物，从而分别得到对NMDA和AMPA受体具有增强的效力和选择性的化合物。因此，
• Solid-Phase Synthesis of Polyamine Toxin Analogues:  Potent and Selective Antagonists of Ca²⁺-Permeable AMPA Receptors
  作者：Hasse Kromann、Sonata Krikstolaityte、Anne J. Andersen、Kim Andersen、Povl Krogsgaard-Larsen、Jerzy W. Jaroszewski、Jan Egebjerg、Kristian Strømgaard

  DOI：10.1021/jm020314s

  日期：2002.12.1

  The wasp toxin philanthotoxin-433 (PhTX-433) is a nonselective and noncompetitive antagonist of ionotropic receptors, such as ionotropic glutamate receptors and nicotinic acetylcholine receptors. Polyamine toxins are extensively used for the characterization of subtypes of ionotropic glutamate receptors, in particular Ca2+-permeable AMPA and kainate receptors. We have previously shown that an analogue of PhTX-433 with one of the amino groups replaced by a methylene group, philanthotoxin-83 (PhTX-83) is a selective and potent antagonist of AMPA receptors. We now describe the solid-phase synthesis of analogues of PhTX-83 and the electrophysiological characterization of these analogues on cloned AMPA and kainate receptors. The polyamine portion of PhTX-83 was modified systematically by chaniging the position. of the. secondary amino group along the polyamine chain. In another series of analogues, the acyl moiety of PhTX-83 was replaced by acids of different size and lipophilicity. Using electrophysiological techniques, PhTX-56 was shown to be a highly potent (K-i = 3.3 +/- 0.78 nM) and voltage-dependent antagonist of homomeric GluR1 receptors and was more than 1000-fold less potent when tested on heteromeric GluR1+GluR2, as well as homomeric GluR5(Q) receptors, thus being selective for Ca2+-permeable AMPA receptors. Variation of the acyl group of PhTX-83 had only minor effect on antagonist potency at homomeric GluR receptors but led to a significant decrease in the voltage-dependence. In conclusion, PhTX-56 is a novel, very potent, and selective antagonist of Ca2+-permeable AMPA receptors and is a promising tool for structure/function studies of the ion channel of the AMPA receptor.
• Uncompetitive Antagonism of AMPA Receptors:  Mechanistic Insights from Studies of Polyamine Toxin Derivatives
  作者：Trine F. Andersen、Denis B. Tikhonov、Ulrik Bølcho、Konstantin Bolshakov、Jared K. Nelson、Florentina Pluteanu、Ian R. Mellor、Jan Egebjerg、Kristian Strømgaard

  DOI：10.1021/jm060606j

  日期：2006.9.1

  Philanthotoxins are uncompetitive antagonists of Ca2+-permeable AMPA receptors presumed to bind to the pore-forming region, but a detailed molecular mechanism for this interaction is missing. Here a small library of novel philanthotoxins was designed and synthesized using a solid-phase strategy. The biological activities were investigated at cloned and "native" AMPA receptors using electrophysiological techniques. A distinct relationship between length of the polyamine moiety and the location of a secondary amino group was observed. Fitting the data to the Woodhull equation allowed the first experimental demonstration of the relative location and orientation of the philanthotoxin molecule in the receptor. These results were corroborated by in silico studies using a homology model of the AMPA receptor ion channel. Together these studies provide strong evidence for a molecular mechanism by which polyamine toxins antagonize the AMPA receptor ion channel and provide the basis for rational development of uncompetitive antagonists of AMPA receptors.
• Dendron-Functionalized Core–Shell Superparamagnetic Nanoparticles: Magnetically Recoverable and Reusable Catalysts for Suzuki CC Cross-Coupling Reactions
  作者：Daniel Rosario-Amorin 、Xin Wang 、Manuel Gaboyard、Rodolphe Clérac 、Sylvain Nlate 、Karine Heuzé

  DOI：10.1002/chem.200901866

  日期：2009.11.23

  dicyclohexyldiphosphino palladium complex was synthesized. The metallodendron was grafted onto core–shell superparamagnetic nanoparticles (γ‐Fe2O3/polymer, 200–500 nm) to give optimal catalytic reactivity in cross‐coupling reactions. The grafted nanoparticles were used as recoverable and reusable catalysts for Suzuki CC cross‐coupling reactions. They showed remarkable reactivity towards iodo‐ and bromoarenes under

  合成了用二环己基二膦基钯配合物官能化的金属十二烷基。所述metallodendron接枝到核-壳纳米颗粒的超顺磁（γ-的Fe 2 ö 3 /聚合物，200-500纳米）的交叉偶联反应以得到最佳的催化活性。接枝的纳米颗粒用作铃木C的可回收和可重复使用的催化剂C交叉偶联反应。它们在温和的条件下对碘和溴代芳烃显示出显着的反应性，对氯代芳烃具有前所未有的反应性。催化反应完成后，通过使用简单的磁体吸引超顺磁性接枝的纳米颗粒，即可轻松回收催化剂。催化剂被回收超过25次，几乎没有明显的反应性损失。
• LIGANDS FOR CAPTURING MICROVESICLES AND USES THEREOF
  申请人：UNIVERSITÉ DE BORDEAUX

  公开号：US20220326228A1

  公开（公告）日：2022-10-13

  The invention relates to ligands able to bind to microvesicles, comprising a plurality of metal(II)-dipicolylamine moieties and their use in the diagnosis or prognostic of disorders in a subject.