4-<(tert-butyldiphenylsilyl)oxy>butyl azide | 166193-97-1

• 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: 4-<(tert-butyldiphenylsilyl)oxy>butyl azide
• 英文别名: 4-Azidobutoxy-tert-butyl-diphenylsilane
• CAS: 166193-97-1
• 化学式: C₂₀H₂₇N₃OSi
• 分子量: 353.539
• InChiKey: BYNMMDIYNJNOLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<(tert-butyldiphenylsilyl)oxy>butyl azide 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到4-叠氮基丁烷-1-醇
  参考文献：
  名称：

  Synthesis of a metabolite of an anti-angiogenic lead candidate based on a d-glucosamine motif

  摘要：

  A rapid synthetic access to ACL 21269 was established in 12 steps starting from thiogylcoside 9 utilizing synthons 8 and 6 to introduce the pharmacophores at positions 1 and 2. The functional groups decorating the glucosamine scaffold were introduced in a particular order and common protecting groups were employed to establish a robust synthetic process. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.009
• 作为产物：
  描述：

  4-((tert-butyldiphenylsilyl)oxy)butan-1-amine 在 4-二甲氨基吡啶 、 triflic azide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 4-<(tert-butyldiphenylsilyl)oxy>butyl azide
  参考文献：
  名称：

  Synthesis of a metabolite of an anti-angiogenic lead candidate based on a d-glucosamine motif

  摘要：

  A rapid synthetic access to ACL 21269 was established in 12 steps starting from thiogylcoside 9 utilizing synthons 8 and 6 to introduce the pharmacophores at positions 1 and 2. The functional groups decorating the glucosamine scaffold were introduced in a particular order and common protecting groups were employed to establish a robust synthetic process. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.009

文献信息

• Synthesis and Biochemical Evaluation of Adenosylspermidine, a Nucleoside-Polyamine Adduct Inhibitor of Spermidine Synthase
  作者：John R. Lakanen、Anthony E. Pegg、James K. Coward

  DOI：10.1021/jm00014a023

  日期：1995.7

  proved to be a very potent inhibitor of that enzyme. Two synthetic routes to effect the coupling of the polyamine spermidine to the nucleoside adenosine were studied. The first route involved a proposed Wittig or Julia olefination reaction to form the critical 5'-6' carbon-carbon bond between the nucleoside and polyamine moieties. This route failed due to a facile beta-elimination of a portion of the side

  研究了新型的多胺生物合成多底物加合物抑制剂的合成。获得了设计用于抑制亚精胺合酶的第一个目标化合物，并证明是该酶的非常有效的抑制剂。研究了影响多胺亚精胺与核苷腺苷偶联的两种合成途径。第一条途径涉及拟议的维蒂希或朱莉娅烯化反应，以在核苷和多胺部分之间形成关键的5'-6'碳-碳键。由于在任一偶联反应过程中从碳负离子中间体中容易除去一部分侧链，导致该路线失败。第二种方法涉及还原胺化方法，并证明是成功的。新的抑制剂，俗称腺苷亚精胺，
• Asymmetric Organocatalytic Intramolecular Aza-Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2-Substituted Piperidines
  作者：Jian-Dong Liu、Ying-Chun Chen、Guo-Biao Zhang、Zhi-Qiang Li、Peng Chen、Ji-Yuan Du、Yong-Qiang Tu、Chun-An Fan

  DOI：10.1002/adsc.201100282

  日期：2011.10

  an achiral Brønsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen-containing carbon center in functionalized 2-substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2-substituted

  通过烯酮氨基甲酸酯的有机催化对映选择性分子内氮杂-迈克尔加成反应已战略性地获得了具有侧酮基的合成有用的功能化2-取代的哌啶，其中烯酮部分作为迈克尔受体和氨基甲酸酯部分作为迈克尔的新型内部底物组合供体在不对称双功能有机催化中被发现。这种杂原子共轭加成反应是通过使用基于手性金鸡纳的手性叔叔二胺和非手性布朗斯台德酸实现的，主要以高收率和良好至优异的立体控制进行（最高ee为99％））。该反应提供了另一种催化不对称方法，用于在功能化的2-取代的哌啶中安装立体异构的含氮碳中心，从而导致了一些天然存在的生物活性的2-取代的哌啶生物碱的直接，快速合成的发展。
• Synthesis of a metabolite of an anti-angiogenic lead candidate based on a d-glucosamine motif
  作者：Latika Singh、Ann Lam、Rajaratnam Premraj、Joachim Seifert

  DOI：10.1016/j.tetlet.2008.06.009

  日期：2008.8

  A rapid synthetic access to ACL 21269 was established in 12 steps starting from thiogylcoside 9 utilizing synthons 8 and 6 to introduce the pharmacophores at positions 1 and 2. The functional groups decorating the glucosamine scaffold were introduced in a particular order and common protecting groups were employed to establish a robust synthetic process. (C) 2008 Elsevier Ltd. All rights reserved.