N-but-3-ynyl-2,2,2-trifluoroacetamide | 669776-70-9

• 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: N-but-3-ynyl-2,2,2-trifluoroacetamide
• 英文别名: N-(but-3-yn-1-yl)-2,2,2-trifluoroacetamide
• CAS: 669776-70-9
• 化学式: C₆H₆F₃NO
• mdl: MFCD19643004
• 分子量: 165.115
• InChiKey: DSJUGXXRENVCSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-but-3-ynyl-2,2,2-trifluoroacetamide 在 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 3'-O-acetyl-5'-O-4,4'-dimethoxytrityl-5-(3''-trifluoroacetamidobutynyl)-2'-deoxycytidine
  参考文献：
  名称：

  带有氨基和硫醇官能团的2'-脱氧胞苷：通过Vent（exo-）聚合酶的合成和掺入。

  摘要：

  [反应：见正文]描述了带有氨基和硫醇基的2'-脱氧胞苷核苷的合成，该核苷通过丁炔基连接基附加到核碱基的5位。然后从核苷合成相应的三磷酸酯，并通过Vent（exo（-））DNA聚合酶掺入寡核苷酸。对于氨基官能化的衍生物，证明了Vent（exo（-））聚合酶在聚合酶链反应（PCR）中扩增包含这些官能化胞苷衍生物的寡核苷酸的能力。

  DOI：

  10.1021/ol0360290
• 作为产物：
  描述：

  三氟乙酸乙酯 、 1-氨基-3-丁炔 以 甲醇 为溶剂， 反应 17.0h， 以92%的产率得到N-but-3-ynyl-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  C8-炔基-和烷基氨基取代的2'-脱氧鸟苷：核酸修饰的通用接头

  摘要：

  修饰的核苷与柔性通用接头的结合对于核酸的合成后修饰具有巨大的价值。因此，首次合成了C8-炔基-和烷基氨基取代的2'-脱氧鸟苷，并将其掺入短的寡核苷酸序列中。讨论了这些C8取代的2'-脱氧鸟苷的顺式构象的偏爱性和双链体的稳定性。还检查了Z-DNA的稳定作用。

  DOI：

  10.1016/j.tet.2008.01.091

文献信息

• Selective radiolabeling of biomolecules
  申请人：General Electric Company

  公开号：EP2591808A2

  公开（公告）日：2013-05-15

  Provided herein are methods for introducing fluorine atom onto a biomolecule comprising: (i) providing a linker comprising a thiol-reactive terminus and an azido/alkyne-reactive terminus; (ii) reacting the thiol-reactive terminus of the linker with a biomolecule comprising at least one thiol group or a reactive derivative thereof; and (iii) subsequently reacting the azido/alkyne-reactive terminus of the linker with a fluorine-substituted azide or alkyne respectively. Also provided are compositions and method of synthesis of bifunctional linkers and bioconjugates as well as radio-diagnostic agents comprising fluorine-labeled biomolecules.

  本文提供了将氟原子引入生物大分子的方法，该方法包括：(i) 提供包含硫醇反应性末端和叠氮/炔反应性末端的连接体；(ii) 将连接体的硫醇反应性末端与包含至少一个硫醇基团或其反应性衍生物的生物大分子反应；(iii) 随后将连接体的叠氮/炔反应性末端分别与氟取代的叠氮化物或炔反应。此外，还提供了双功能连接体和生物结合剂的组合物和合成方法，以及包含氟标记生物大分子的放射诊断剂。
• SELECTIVE RADIOLABELING OF BIOMOLECULES
  申请人：Padilla De Jesus Omayra Liz

  公开号：US20080161537A1

  公开（公告）日：2008-07-03

  Provided herein are methods for introducing fluorine atom onto a biomolecule comprising: (i) providing a linker comprising a thiol-reactive terminus and an azido/alkyne-reactive terminus; (ii) reacting the thiol-reactive terminus of the linker with a biomolecule comprising at least one thiol group or a reactive derivative thereof; and (iii) subsequently reacting the azido/alkyne-reactive terminus of the linker with a fluorine-substituted azide or alkyne respectively. Also provided are compositions and method of synthesis of bifunctional linkers and bioconjugates as well as radio-diagnostic agents comprising fluorine-labeled biomolecules.
• [EN] SELECTIVE RADIOLABELING OF BIOMOLECULES<br/>[FR] RADIOMARQUAGE SÉLECTIF DE BIOMOLÉCULES
  申请人：GEN ELECTRIC

  公开号：WO2009080561A1

  公开（公告）日：2009-07-02

  Provided herein are methods for introducing flυorine atom onto a biomolecule comprising: (i) providing a linker comprising a thiol-reactive teminus and an azido/alkyne-reactive terminus; (ii) reacting the thiol-reactive terminus of the linker with a biomolecule comprising at least one thiol group or a reactive derivative thereof; and (iii) subsequently reacting the azido/alkyne-reactive terminus of the linker with a fluorine-substituted azide or alkyne respectively. Also provided are compositions and method of synthesis of bifunctional linkers and bioconjugates as well as radio-diagnostic agents comprising fluorine-labeled biomolecules.
• 2‘-Deoxycytidines Carrying Amino and Thiol Functionality:  Synthesis and Incorporation by Vent (Exo^-) Polymerase
  作者：Abhijit Roychowdhury、Heshan Illangkoon、Cynthia L. Hendrickson、Steven A. Benner

  DOI：10.1021/ol0360290

  日期：2004.2.1

  [reaction: see text] The synthesis of 2'-deoxycytidine nucleosides bearing amino and thiol groups appended to the 5-position of the nucleobase via a butynyl linker is described. The corresponding triphosphates were then synthesized from the nucleoside and incorporated into oligonucleotides by Vent (exo(-)) DNA polymerase. The ability of Vent (exo(-)) polymerase to amplify oligonucleotides containing

  [反应：见正文]描述了带有氨基和硫醇基的2'-脱氧胞苷核苷的合成，该核苷通过丁炔基连接基附加到核碱基的5位。然后从核苷合成相应的三磷酸酯，并通过Vent（exo（-））DNA聚合酶掺入寡核苷酸。对于氨基官能化的衍生物，证明了Vent（exo（-））聚合酶在聚合酶链反应（PCR）中扩增包含这些官能化胞苷衍生物的寡核苷酸的能力。
• C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines: a universal linker for nucleic acids modification
  作者：Yoshio Saito、Katsuhiko Matsumoto、Subhendu Sekhar Bag、Shinzi Ogasawara、Kenzo Fujimoto、Kazuo Hanawa、Isao Saito

  DOI：10.1016/j.tet.2008.01.091

  日期：2008.4

  Incorporation of modified nucleosides with a flexible universal linker is of great value for post-synthetic modification of nucleic acids. Thus, C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines were synthesized for the first time and incorporated into short oligonucleotide sequences. The preference for syn conformation of these C8-substituted 2′-deoxyguanosines and the stability of the duplexes

  修饰的核苷与柔性通用接头的结合对于核酸的合成后修饰具有巨大的价值。因此，首次合成了C8-炔基-和烷基氨基取代的2'-脱氧鸟苷，并将其掺入短的寡核苷酸序列中。讨论了这些C8取代的2'-脱氧鸟苷的顺式构象的偏爱性和双链体的稳定性。还检查了Z-DNA的稳定作用。