1,8-Naphthyridine-3-acetic acid, 1,2,7,8-tetrahydro-2,7-dioxo- | 216678-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,8-Naphthyridine-3-acetic acid, 1,2,7,8-tetrahydro-2,7-dioxo-
• 英文别名: (1,8-naphthyridin-2,7-(1,8H)-dion-3-yl)acetic acid
• CAS: 216678-86-3
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: QCBLIMLQLUDFPN-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  855.7±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  103.02
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,8-Naphthyridine-3-acetic acid, 1,2,7,8-tetrahydro-2,7-dioxo- 在 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 N-((1,8-naphthyridine-2,7(1,8H)-dion-3-yl)acetyl-N-(2-tert-butyloxycarbonyl)aminoethyl)glycine
  参考文献：
  名称：

  1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

  摘要：

  A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7degreesC per unit) or pseudoisocytosine (1.5degreesC per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions (similar to3degreesC per unit). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00658-3
• 作为产物：
  描述：

  (7-chloro-1,8-naphthyridin-2(1H)-on-3-yl)acetic acid 在 sodium hydroxide 作用下， 反应 19.0h， 以94%的产率得到1,8-Naphthyridine-3-acetic acid, 1,2,7,8-tetrahydro-2,7-dioxo-
  参考文献：
  名称：

  1,8-Naphthyridin-2,7-(1,8H)-dione is an effective mimic of protonated cytosine in peptide nucleic acid triplex recognition systems

  摘要：

  A novel bicyclic mimic of protonated cytosine [1,8-naphthyridin-2,7-(1,8H)-dione, (K)] for Hoogsteen type triplex recognition of guanine has been designed for incorporation into peptide nucleic acids. Bis-PNA clamps with the K base incorporated in the Hoogsteen strand showed a significant stabilization of the triplexes at pH 7 as compared to similar triplexes with PNA oligomers containing either cytosine (6.7degreesC per unit) or pseudoisocytosine (1.5degreesC per unit). Cooperative stabilization was observed when the K units were placed in adjacent positions (similar to3degreesC per unit). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00658-3