1-butyl-3,3-dimethyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-5-((trimethylsilyl)ethynyl)-3H-indol-1-ium iodide | 1354932-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-butyl-3,3-dimethyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-5-((trimethylsilyl)ethynyl)-3H-indol-1-ium iodide
• CAS: 1354932-53-8
• 化学式: C₃₃H₄₃N₂Si*I
• 分子量: 622.708
• InChiKey: VVNVLZHZSUOGPF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-butyl-3,3-dimethyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-5-((trimethylsilyl)ethynyl)-3H-indol-1-ium iodide 在 四丁基氟化铵 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到1-butyl-5-ethynyl-3,3-dimethyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-3H-indol-1-ium iodide
  参考文献：
  名称：

  Efficient reverse click labeling of azide oligonucleotides with multiple alkynyl Cy-Dyes applied to the synthesis of HyBeacon probes for genetic analysis

  摘要：

  A convenient method of oligonucleotide labeling using click chemistry has been developed. A 2'-mesyloxyethyl ribothymidine phosphoramidite monomer was incorporated into DNA at several loci during solid phase oligonucleotide synthesis and converted to 2'-azidoethyl ribothymidine in high yield on the synthesis resin. The resultant azide oligonucleotides were doubly and triply labeled with alkynemodified cyanine dyes and their biophysical properties were studied. The influence of the dye structures and method of labeling on the fluorescence properties of the DNA probes is discussed and compared with a standard labeling method using active esters of Cy-Dyes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.041
• 作为产物：
  描述：

  1-butyl-5-iodo-3,3-dimethyl-2-[(E)-2-(phenylamino)ethenyl]-3H-indolium iodide 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 乙酸酐 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 1-butyl-3,3-dimethyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-en-1-yl)-5-((trimethylsilyl)ethynyl)-3H-indol-1-ium iodide
  参考文献：
  名称：

  Efficient reverse click labeling of azide oligonucleotides with multiple alkynyl Cy-Dyes applied to the synthesis of HyBeacon probes for genetic analysis

  摘要：

  A convenient method of oligonucleotide labeling using click chemistry has been developed. A 2'-mesyloxyethyl ribothymidine phosphoramidite monomer was incorporated into DNA at several loci during solid phase oligonucleotide synthesis and converted to 2'-azidoethyl ribothymidine in high yield on the synthesis resin. The resultant azide oligonucleotides were doubly and triply labeled with alkynemodified cyanine dyes and their biophysical properties were studied. The influence of the dye structures and method of labeling on the fluorescence properties of the DNA probes is discussed and compared with a standard labeling method using active esters of Cy-Dyes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.041