N-trifluoroacetyl-(6-aminohexyl)-1-tosylate | 51224-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-trifluoroacetyl-(6-aminohexyl)-1-tosylate
• 英文别名: 6-(2,2,2-trifluoroacetamido)hexyl 4-methylbenzenesulfonate；6-(2,2,2-Trifluoroacetamido)hexyl 4-methylbenzene-1-sulfonate；6-[(2,2,2-trifluoroacetyl)amino]hexyl 4-methylbenzenesulfonate
• CAS: 51224-09-0
• 化学式: C₁₅H₂₀F₃NO₄S
• 分子量: 367.389
• InChiKey: OKGCSXVPKOIXMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetyl-(6-aminohexyl)-1-tosylate 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(6-trifluoroacetamido)hexyluridine
  参考文献：
  名称：

  Zwitterionic Oligonucleotides: A Study on Binding Properties of 2′-O-Aminohexyl Modifications

  摘要：

  2'-O-Aminohexyl side chains provide excellent conditions for zwitterionic interstrand and intrastrand interactions of oligonucleolides. 2'-O-Aminoalkylatedphosphoramidites of adenosine and uridine were synthesized and incorporated in increasing number into homo adenosine and homo uridine/thymidine dodecamers, respectively. CD spectra of these dodecamers with complementary sense DNA exhibited a B-DNA type structure. While duplex stability values of all tested oligonucleotides were lower than those Of the native oligonucleotides, they were significantly higher than those of 2'-O-heptyl modified oligonucleotides. The destabilization amounted to 0.9, 1.5, and 2.7 degrees C per modification for 2'-O-aminohexyl adenosine, 2'-O-aminohexyl uridine, and 2'-O-heptyl adenosine substitutions. These findings are pointing to a duplex stabilizing effect of the interaction of side chain amino groups with backbone phosphoric acid.

  DOI：

  10.1081/ncn-200067400
• 作为产物：
  描述：

  6-氨基-1-己醇 以 水 为溶剂， 生成 N-trifluoroacetyl-(6-aminohexyl)-1-tosylate
  参考文献：
  名称：

  糖苷配基末端具有氨基的1-硫代醛糖苷的合成

  摘要：

  摘要由d-半乳糖，d-葡萄糖和2-氨基-2-deoxy-d-葡萄糖的乙酰化1-卤化物直接或间接制备了许多1-thio-β-d-醛糖苷。这些醛糖苷在糖苷配基的末端具有氨基，其形式为6-氨基己基，6-氨基己基或对氨基苯基。

  DOI：

  10.1016/s0008-6215(00)86198-4

文献信息

• Synthesis of 1-thioaldosides having an amino group at the aglycon terminal
  作者：Stefan Chipowsky、Chuan Lee Yuan

  DOI：10.1016/s0008-6215(00)86198-4

  日期：1973.12

  prepared, directly or indirectly, from acetylated 1-halides of d -galactose, d -glucose, and 2-amino-2-deoxy- d -glucose. These aldosides have an amino group at the terminal position of the aglycon, in the form of 6-aminohexyl, 6-aminohexanoyl, or p-aminophenyl groups.

  摘要由d-半乳糖，d-葡萄糖和2-氨基-2-deoxy-d-葡萄糖的乙酰化1-卤化物直接或间接制备了许多1-thio-β-d-醛糖苷。这些醛糖苷在糖苷配基的末端具有氨基，其形式为6-氨基己基，6-氨基己基或对氨基苯基。
• Site-Selective Defluorinative sp³ C–H Alkylation of Secondary Amides
  作者：Wen-Jun Yue、Craig S. Day、Ruben Martin

  DOI：10.1021/jacs.1c03126

  日期：2021.5.5
• NOVEL COMPOUNDS
  申请人：QBI ENTERPRISES LTD.

  公开号：US20160152979A1

  公开（公告）日：2016-06-02

  Disclosed herein are novel compounds having the general formula (I): Q-L-A1  (I) wherein Q is a Q10 moiety, such as ubiquinone; L, which is optionally included, is a linker selected from the group consisting of polyesters, polyethers, polyamines, polyamides, peptides, carbohydrates, lipids, C 3-12 alkyl straight chain based linkers, polyethylene glycols and other polymeric compounds; and A1 is a nucleotide moiety. Disclosed are also pharmaceutical compositions comprising such compounds or pharmaceutically acceptable salts thereof. Further disclosed is the use of such compounds in the treatment of cancer and/or a cancer related medical condition.
• Zwitterionic Oligonucleotides: A Study on Binding Properties of 2′-<i>O</i>-Aminohexyl Modifications
  作者：Christian R. Noe、Johannes Winkler、Ernst Urban、Matthias Gilbert、Georg Haberhauer、Helmut Brunar

  DOI：10.1081/ncn-200067400

  日期：2005.7.1

  2'-O-Aminohexyl side chains provide excellent conditions for zwitterionic interstrand and intrastrand interactions of oligonucleolides. 2'-O-Aminoalkylatedphosphoramidites of adenosine and uridine were synthesized and incorporated in increasing number into homo adenosine and homo uridine/thymidine dodecamers, respectively. CD spectra of these dodecamers with complementary sense DNA exhibited a B-DNA type structure. While duplex stability values of all tested oligonucleotides were lower than those Of the native oligonucleotides, they were significantly higher than those of 2'-O-heptyl modified oligonucleotides. The destabilization amounted to 0.9, 1.5, and 2.7 degrees C per modification for 2'-O-aminohexyl adenosine, 2'-O-aminohexyl uridine, and 2'-O-heptyl adenosine substitutions. These findings are pointing to a duplex stabilizing effect of the interaction of side chain amino groups with backbone phosphoric acid.