1-Trimethylsilylhex-1-yn-3-yl methanesulfonate | 913618-99-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-Trimethylsilylhex-1-yn-3-yl methanesulfonate
• 英文别名: 1-trimethylsilylhex-1-yn-3-yl methanesulfonate
• CAS: 913618-99-2
• 化学式: C₁₀H₂₀O₃SSi
• 分子量: 248.418
• InChiKey: DVEMSWQBHPNPEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Trimethylsilylhex-1-yn-3-yl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到3-Azidohex-1-ynyl(trimethyl)silane
  参考文献：
  名称：

  Synthesis of azide-alkyne fragments for ‘click’ chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols

  摘要：

  A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazolebased peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.131
• 作为产物：
  描述：

  lithium trimethylsilylacetylenide 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-Trimethylsilylhex-1-yn-3-yl methanesulfonate
  参考文献：
  名称：

  Synthesis of azide-alkyne fragments for ‘click’ chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols

  摘要：

  A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazolebased peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.131

文献信息

• Silicon-Induced Phenanthrene Formation from Benzynes and Allenylsilanes
  作者：Jih Ru Hwu、Sharada P. Swain

  DOI：10.1002/chem.201203738

  日期：2013.5.17

  Now directly feasible: The silicon atom in allenylsilanes enabled their reaction with two equivalents of benzynes to generate (α‐phenanthrenyl)vinylsilanes in good to excellent yields through an unprecedented [2+2+2] pathway (see scheme).

  现在直接可行：烯丙基硅烷中的硅原子能够使其与两当量的苯炔反应，以前所未有的[2 + 2 + 2]途径生成（α-菲基）乙烯基硅烷，收率高至优异（参见方案）。
• Re-orienting coupling of organocuprates with propargyl electrophiles from S_N2′ to S_N2 with stereocontrol
  作者：Barry M. Trost、Laurent Debien

  DOI：10.1039/c6sc01086e

  日期：——

  Diorganocuprate(i) reagents derived from lithiated heterocycles and CuCN react with enantioenriched secondary propagryl bromides to give the corresponding propargylated heterocycles.

  从锂化杂环和CuCN衍生的Diorganocuprate(i)试剂与手性丰富的二级丙炔基溴化物反应，得到相应的丙炔基化杂环化合物。
• Synthesis of azide-alkyne fragments for ‘click’ chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols
  作者：Oliver D. Montagnat、Guillaume Lessene、Andrew B. Hughes

  DOI：10.1016/j.tetlet.2006.07.131

  日期：2006.9

  A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further 'click' reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazolebased peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery. (c) 2006 Elsevier Ltd. All rights reserved.