4-[N-(2,2,2-trifluoroacetyl)amino]butan-1-ol | 168091-94-9

• 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: 4-[N-(2,2,2-trifluoroacetyl)amino]butan-1-ol
• 英文别名: 4-(N-Methyl-trifluoroacetamido)-1-butanol；4-(N-Methyl-trifluoracetamido)-1-butanol；2,2,2-trifluoro-N-(4-hydroxybutyl)-N-methylacetamide
• CAS: 168091-94-9
• 化学式: C₇H₁₂F₃NO₂
• 分子量: 199.173
• InChiKey: CPLCDLBGCIEJLU-UHFFFAOYSA-N

物化性质

• 沸点：
  276.2±40.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[N-(2,2,2-trifluoroacetyl)amino]butan-1-ol 在 吡啶 、 ammonium hydroxide 作用下， 反应 0.5h， 生成 1-甲基吡咯烷
  参考文献：
  名称：

  The 4-[N-Methyl-N-(2,2,2-trifluoroacetyl)amino]butyl Group as an Alternative to the 2-Cyanoethyl Group for Phosphate Protection in the Synthesis of Oligodeoxyribonucleotides

  摘要：

  The 4-[N-methyl-N-(2,2,2-trifluoroacetyl)amino]butyl group for phosphate protection in the synthesis of oligodeoxyribonucleotides has been developed to completely prevent nucleobase alkylation by acrylonitrile that could potentially occur upon deprotection of the traditional 2-cyanoethyl phosphate protecting group. The properties of this new phosphate protecting group were evaluated using the model phosphotriester 9. The mechanism of phosphate deprotection was studied by treating 9 with concentrated NH4OH. NMR analysis,of the deprotection reaction demonstrated that cleavage of the N-trifluoroacetyl group is rate-limiting. The resulting phosphotriester intermediate 13 was also shown to undergo rapid cyclodeesterification to produce O,O-diethyl phosphate 15 and N-methylpyrrolidine -16 (Scheme 2). Given the facile removal of the 4-[N-methyl-N-(2,2,2-trifluoroacetyl)amino]butyl phosphate protecting group under mild basic conditions, its utilization in oligonucleotide synthesis began with the preparation of the deoxyribonucleoside phosphoramidites 4a-d (Scheme 3). The coupling efficiency of 4a-d and conventional a-cyanoethyl deoxyribonucleoside phosphoramidites 24a-d was then compared in the solid-phase synthesis of the 20-mer d(ATCCGTAGCTAAGGTCATGC). As previously observed in the deprotection of 9, the 4-[N-methyl,N-(2,2,2-trifluoroacetyl)amino]butyl phosphate protecting groups were easily and completely removed from the oligonucleotide by using either concentrated NH4OH or pressurized ammonia gas. Analysis of the deprotected oligomer by polyacrylamide gel electrophoresis (Figure 3) indicated that the phosphoramidites 4a-d are as efficient as the 2-cyanoethyl phosphoramidites 24a-d in the synthesis of the 20-mer. Furthermore, following digestion of the crude 20-mer by snake venom phosphodiesterase and bacterial alkaline phosphatase, HPLC analysis showed complete hydrolysis to individual nucleosides and no detectable nucleobase modification.

  DOI：

  10.1021/jo990835w
• 作为产物：
  描述：

  三氟乙酸乙酯 以 甲醇 为溶剂， 以96%的产率得到4-[N-(2,2,2-trifluoroacetyl)amino]butan-1-ol
  参考文献：
  名称：

  Hepatic-directed compounds and reagents for preparation thereof

  摘要：

  肝向化合物、制备此类化合物的有用试剂以及相关方法和组合物进行了讨论。肝向化合物通过代谢机制进行处理，这些代谢机制通常在程度或种类上与非肝向化合物所遇到的代谢机制不同。用于制备肝向化合物的有用试剂包括具有多个连接成迭代分支配置的己糖残基的己糖簇。在一个实施例中，己糖簇包括至少四个己糖残基，每个配置的分支具有两个叉。在另一个实施例中，己糖簇包括至少九个己糖残基，每个配置的分支具有三个叉。

  公开号：

  US05886143A1

文献信息

• Radiolabeled annexin conjugates with hexose and a chelator
  申请人：NeoRx Corporation

  公开号：US05968477A1

  公开（公告）日：1999-10-19

  Radiolabeled annexin and modified annexin conjugates useful for imaging vascular thrombi are described. Methods for making and using such radiolabeled annexin conjugates are also provided.

  放射性标记的凋亡素和修饰的凋亡素共轭物可用于成像血管血栓。还提供了制备和使用这种放射性标记的凋亡素共轭物的方法。
• Small molecular weight ligand-hexose containing clearing agents
  申请人：NeoRx Corporation

  公开号：US06075010A1

  公开（公告）日：2000-06-13

  Small molecule weight clearing agents containing ligands such as biotin or biotin analogs and hexose residue, in particular galactose or N-acetyl galactosamine residues are taught. These clearing agents effectively clear anti-ligand containing conjugates in vivo via hepatocyte receptor mediated clearance mechanisms.

  含有生物素或生物素类似物和六碳糖残基，特别是半乳糖或N-乙酰半乳糖氨基残基的小分子重量清除剂被教授。这些清除剂通过肝细胞受体介导的清除机制有效地清除体内含有抗配体的结合物。
• Radiolabeled annexins
  申请人：NeoRx Corporation

  公开号：US20030220233A1

  公开（公告）日：2003-11-27

  Radiolabeled annexin and modified annexin conjugates useful for imaging vascular thrombi are described. Methods for making and using such radiolabeled annexin conjugates are also provided.

  本文描述了用于成像血管血栓的放射标记的Annexin和修饰的Annexin结合物。还提供了制备和使用这种放射性标记的Annexin结合物的方法。
• Pretargeting methods and compounds
  申请人：NeoRx Corporation

  公开号：US20030129191A1

  公开（公告）日：2003-07-10

  Methods, compounds, compositions and kits that relate to pretargeted delivery of diagnostic and therapeutic agents are disclosed. In particular, methods for radiometal labeling of biotin, as well as related compounds, are described. Clearing agents and clearance mechanisms are also discussed.

  本发明涉及与预定位递送诊断和治疗剂有关的方法、化合物、组合物和试剂盒。具体而言，描述了生物素的放射金属标记方法及相关化合物。还讨论了清除剂和清除机制。
• Methods of using hepatic-directed compounds in pretargeting strategies
  申请人：NeoRx Corporation

  公开号：US05985826A1

  公开（公告）日：1999-11-16

  Hepatic-directed compounds, reagents useful in making such compounds and associated methods and compositions are disclosed. Hepatic-directed compounds are processed by metabolic mechanisms, which generally differ in degree or in kind from the metabolic mechanisms encountered by compounds which are not so directed. Hepatic-directed compounds useful in the methods disclosed include a hexose cluster characterized by multiple hexose residues connected in an iteratively branched configuration. In one embodiment, the hexose cluster comprises at least four hexose residues with each branch of the configuration having two prongs. In another embodiment, the hexose cluster comprises at least nine hexose residues with each branch of the configuration having three prongs.

  本发明揭示了肝定向化合物、制备这种化合物的试剂以及相关的方法和组合物。肝定向化合物通过代谢机制进行处理，这些代谢机制通常在程度或种类上与不定向化合物所遇到的代谢机制不同。在所揭示的方法中有用的肝定向化合物包括一种由多个六糖残基连接成迭代分支配置的六糖簇。在一个实施例中，六糖簇包括至少四个六糖残基，每个配置的分支具有两个叉。在另一个实施例中，六糖簇包括至少九个六糖残基，每个配置的分支具有三个叉。