6-(trimethylsilyl)hex-5-yn-1-amine | 1365478-24-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-(trimethylsilyl)hex-5-yn-1-amine
• 英文别名: 6-(Trimethylsilyl)hex-5-yn-1-amine；6-trimethylsilylhex-5-yn-1-amine
• CAS: 1365478-24-5
• 化学式: C₉H₁₉NSi
• 分子量: 169.342
• InChiKey: XEDINXQREDNUFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  200.0±23.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(trimethylsilyl)hex-5-yn-1-amine 在 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 2.08h， 生成 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(4-{1-[(6-nitro-1H-indol-3-yl)methyl]-1H-1,2,3-triazol-4-yl}butyl)cyclohexanecarboxamide
  参考文献：
  名称：

  Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach

  摘要：

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.

  DOI：

  10.1021/ja4029582
• 作为产物：
  描述：

  6-三甲基硅烷基-己-5-炔-1-醇 在 sodium azide 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-(trimethylsilyl)hex-5-yn-1-amine
  参考文献：
  名称：

  Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach

  摘要：

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.

  DOI：

  10.1021/ja4029582

文献信息

• A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
  作者：Benjamin Zelenay、Peter Munton、Xiaojie Tian、Silvia Díez-González

  DOI：10.1002/ejoc.201900701

  日期：2019.8.7

  The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalysts was also found active in intermolecular aza-Michael reactions.

  介绍了一种简单的市售铜盐 [Cu(NCMe)4](BF4) 在炔烃和丙二烯的分子内加氢胺化反应中的活性。在空气存在下，在工业乙腈中成功进行了反应。虽然烯烃加氢胺化的尝试失败了，但也发现这种催化剂在分子间氮杂-迈克尔反应中具有活性。
• [EN] E-SELECTIN ANTAGONISTS<br/>[FR] ANTAGONISTES DE L'E-SÉLECTINE
  申请人：GLYCOMIMETICS INC

  公开号：WO2012037034A1

  公开（公告）日：2012-03-22

  Compounds, compositions and methods are provided for inhibiting in vitro and in vivo processes mediated by E-selectin binding. More specifically, particular glycomimetic compounds are described, wherein the compounds are E- selectin antagonists.

  提供了抑制E-选择素结合介导的体内外过程的化合物、组合物和方法。更具体地，描述了特定的糖类拟态化合物，其中这些化合物是E-选择素拮抗剂。
• Correlation between Functionality Preference of Ru Carbenes and <i>exo</i>/<i>endo</i> Product Selectivity for Clarifying the Mechanism of Ring-Closing Enyne Metathesis
  作者：Ok Suk Lee、Kyung Hwan Kim、Jinwoo Kim、Kuktae Kwon、Taedong Ok、Hyotcherl Ihee、Hee-Yoon Lee、Jeong-Hun Sohn

  DOI：10.1021/jo401420f

  日期：2013.9.6

  Functionality preferences of metathesis Ru carbenes to various alkenes and alkynes with electronic and steric diversity were determined by using time-dependent fluorescence quenching. The functionality preferences depend not only on the properties of multiple bonds but also on the ligands on Ru. There was a good correlation between functionality preference and the metathesis reaction outcome. The correlation between functionality preference and exo/endo product ratio offers a solution to resolve the mechanistic issue related with alkene- vs alkyne-initiated pathway in ring-closing enyne metathesis. The correlation indicates the preference is likely to dictate the reaction pathway and eventually the outcome of the reaction. The Ru catalyst favoring alkyne over alkene provides more endo product, indicating that the reaction mainly initiates at the alkyne. By changing the substitution pattern, the preference can be reversed to give an exclusive exo product.
• Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach
  作者：Jonas Egger、Céline Weckerle、Brian Cutting、Oliver Schwardt、Said Rabbani、Katrin Lemme、Beat Ernst

  DOI：10.1021/ja4029582

  日期：2013.7.3

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.