3-(3-Chloro-propoxy)-naphthalene-2-carbonyl chloride | 161603-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(3-Chloro-propoxy)-naphthalene-2-carbonyl chloride
• CAS: 161603-14-1
• 化学式: C₁₄H₁₂Cl₂O₂
• 分子量: 283.154
• InChiKey: PDAOMDGDFOPYBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(3-Chloro-propoxy)-naphthalene-2-carbonyl chloride 在 sodium tetrahydroborate 、 三甲基氰硅烷 、 potassium tert-butylate 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 C₂₇H₂₉N₃O₆
  参考文献：
  名称：

  Synthesis and activity of conformationally-constrained macrocyclic norstatine-based inhibitors of HIV protease

  摘要：

  Two diastereomers of a macrocyclic hydroxyamide (norstatine-based) peptide, having an 18-membered ring system, have been synthesized as HIV protease inhibitors. The (R)-diastereomer (IC50 19 nM) was similar to 17-fold weaker than an acyclic analog, but had comparable or better antiviral activity, suggesting improved cell penetration properties and/or resistance to cellular enzymes for the macrocyclic inhibitor.

  DOI：

  10.1016/0960-894x(96)00034-0
• 作为产物：
  描述：

  3-(3-Hydroxy-propoxy)-naphthalene-2-carboxylic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到3-(3-Chloro-propoxy)-naphthalene-2-carbonyl chloride
  参考文献：
  名称：

  Synthesis and activity of conformationally-constrained macrocyclic norstatine-based inhibitors of HIV protease

  摘要：

  Two diastereomers of a macrocyclic hydroxyamide (norstatine-based) peptide, having an 18-membered ring system, have been synthesized as HIV protease inhibitors. The (R)-diastereomer (IC50 19 nM) was similar to 17-fold weaker than an acyclic analog, but had comparable or better antiviral activity, suggesting improved cell penetration properties and/or resistance to cellular enzymes for the macrocyclic inhibitor.

  DOI：

  10.1016/0960-894x(96)00034-0