3-(十六基氨基)丙腈 | 36341-65-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-(十六基氨基)丙腈
• 英文名称: N-hexadecyl-β-alanine nitrile
• 英文别名: N-Hexadecyl-β-alanin-nitril；3-(hexadecylamino)propiononitrile；3-Hexadecylamino-propionsaeurenitril；N-Hexadecyl-3-aminopropionitril；3-(hexadecylamino)propanenitrile
• CAS: 36341-65-8
• 化学式: C₁₉H₃₈N₂
• 分子量: 294.524
• InChiKey: HURZPRHLIMBWPK-UHFFFAOYSA-N

物化性质

• 熔点：
  39-43 °C
• 沸点：
  174-176 °C
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3-(十六基氨基)丙腈 在 乙醇 、 镍 作用下， 90.0 ℃ 、1.96 MPa 条件下， 生成 N1-十六基-1,3-丙二胺
  参考文献：
  名称：

  Sakakibara et al., Yukagaku/Journal of Japan Oil Chemists' Society, 1957, vol. 6, p. 263,265

  摘要：

  DOI：
• 作为产物：
  描述：

  十六胺 、 丙烯腈 以 甲醇 为溶剂， 反应 15.0h， 生成 3-(十六基氨基)丙腈
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines

  摘要：

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.055

文献信息

• Aliphatic amines as antipityrosporum agents
  作者：Harold Dixon、Norman J. Van Abbe、John K. Sugden

  DOI：10.1021/jm00272a028

  日期：1972.2
• Sakakibara et al., Yukagaku/Journal of Japan Oil Chemists' Society, 1957, vol. 6, p. 263,265
  作者：Sakakibara et al.

  DOI：——

  日期：——
• Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines
  作者：Anurupa Shrestha、Diptesh Sil、Subbalakshmi S. Malladi、Hemamali J. Warshakoon、Sunil A. David

  DOI：10.1016/j.bmcl.2009.03.055

  日期：2009.5

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.