N-ethyl-N-(2-hydroxy-ethyl)-β-alanine nitrile | 854680-20-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-ethyl-N-(2-hydroxy-ethyl)-β-alanine nitrile
• 英文别名: N-Aethyl-N-(2-hydroxy-aethyl)-β-alanin-nitril；3-[Aethyl-(2-hydroxy-aethyl)-amino]-propionsaeure-nitril；3-[Aethyl-(2-hydroxy-aethyl)-amino]-propionitril；3-[Ethyl(2-hydroxyethyl)amino]propanenitrile
• CAS: 854680-20-9
• 化学式: C₇H₁₄N₂O
• mdl: MFCD11914323
• 分子量: 142.201
• InChiKey: JOGVCMRQCJYZPI-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C(Press: 0.2 Torr)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-(2-hydroxy-ethyl)-β-alanine nitrile 在 镍 作用下， 生成 2-[(2-aminopropyl)(ethyl)amino]ethanol
  参考文献：
  名称：

  Burckhalter et al., Journal of the American Chemical Society, 1943, vol. 65, p. 2013

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴丙腈 、 N-乙基乙醇胺 反应 0.5h， 生成 N-ethyl-N-(2-hydroxy-ethyl)-β-alanine nitrile
  参考文献：
  名称：

  Synthesis and DNA-sequence selectivity of a series of mono- and difunctional 9-aminoacridine nitrogen mustards

  摘要：

  The aim of this work was to identify nitrogen mustards that would react selectively with DNA, particularly in G-rich regions. A sei ies of mono- and difunctional nitrogen mustards was synthesized in which the (2-chloroethyl)amino functions were connected to the N-9 of 9-aminoacridine by way of a spacer chain consisting of two to six methylene units. The length of the spacer chain connecting the alkylating and putative DNA-intercalating groups was found to affect the preference for the alkylation of different guanine-N-7 positions in a DNA sequence. All of the compounds reacted preferentially at G's that are followed by G as do most other types of nitrogen mustards, but the degree of selectivity was greater. The compounds reacted at much lower concentrations than were required for comparable reaction by mechlorethamine (HN2), consistent with initial noncovalent binding to DNA prior to guanine-N-7 alkylation. The degree of DNA-sequence selectivity increased as the spacer-chain length decreased below four methylene units. Most strikingly, long spacer compounds reacted strongly at 5'-GT-3' sequences, Whereas this reaction was almost completely suppressed when-the spacer length was reduced to two or three methylenes. Mono- and difunctional compounds of a given spacer length showed no consistent difference in DNA-sequence preference.

  DOI：

  10.1021/jm00027a008

文献信息

• The Preparation of 7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1- methylbutylamino)-quinoline and Related Compounds
  作者：Alexander R. Surrey、Henry F. Hammer

  DOI：10.1021/ja01160a116

  日期：1950.4
• Burckhalter et al., Journal of the American Chemical Society, 1943, vol. 65, p. 2013
  作者：Burckhalter et al.

  DOI：——

  日期：——
• Synthesis and DNA-sequence selectivity of a series of mono- and difunctional 9-aminoacridine nitrogen mustards
  作者：Kurt W. Kohn、Ann Orr、Patrick M. O'Connor、Lynn James Guziec、Frank S. Guziec

  DOI：10.1021/jm00027a008

  日期：1994.1

  The aim of this work was to identify nitrogen mustards that would react selectively with DNA, particularly in G-rich regions. A sei ies of mono- and difunctional nitrogen mustards was synthesized in which the (2-chloroethyl)amino functions were connected to the N-9 of 9-aminoacridine by way of a spacer chain consisting of two to six methylene units. The length of the spacer chain connecting the alkylating and putative DNA-intercalating groups was found to affect the preference for the alkylation of different guanine-N-7 positions in a DNA sequence. All of the compounds reacted preferentially at G's that are followed by G as do most other types of nitrogen mustards, but the degree of selectivity was greater. The compounds reacted at much lower concentrations than were required for comparable reaction by mechlorethamine (HN2), consistent with initial noncovalent binding to DNA prior to guanine-N-7 alkylation. The degree of DNA-sequence selectivity increased as the spacer-chain length decreased below four methylene units. Most strikingly, long spacer compounds reacted strongly at 5'-GT-3' sequences, Whereas this reaction was almost completely suppressed when-the spacer length was reduced to two or three methylenes. Mono- and difunctional compounds of a given spacer length showed no consistent difference in DNA-sequence preference.