1-benzyloxy-3-(bicyclo[2.2.1]hept-2-ylamino)propan-2-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-benzyloxy-3-(bicyclo[2.2.1]hept-2-ylamino)propan-2-ol
• 英文别名: 1-(2-Bicyclo[2.2.1]heptanylamino)-3-phenylmethoxypropan-2-ol
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: AUYRNAPSRRTKGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄基缩水甘油醚 、 双环[2.2.1]-2-庚胺 以 乙醇 为溶剂， 140.0 ℃ 、344.75 kPa 条件下， 反应 0.07h， 以95%的产率得到1-benzyloxy-3-(bicyclo[2.2.1]hept-2-ylamino)propan-2-ol
  参考文献：
  名称：

  Microwave-Assisted Ring Opening of Epoxides:  A General Route to the Synthesis of 1-Aminopropan-2-ols with Anti Malaria Parasite Activities

  摘要：

  A series of 1-aminopropan-2-ols were synthesized and evaluated against two strains of malaria, Plasmodium falciparum FCR3 (chloroquine-resistant) and 3D7 (chloroquine-sensitive). Microwave-assisted ring opening of epoxides (aryl and alkyl glycidyl ethers, glycidol, epichlorohydrin) with various amines without catalysts generated the desired library of beta-amino alcohols rapidly and efficiently. Most of the compounds showed micromolar potency against malaria, with seven of them having IC50 values between 1 and 10 mu M against both Plasmodium falciparum strains.

  DOI：

  10.1021/jm070553l

文献信息

• Microwave-Assisted Ring Opening of Epoxides:  A General Route to the Synthesis of 1-Aminopropan-2-ols with Anti Malaria Parasite Activities
  作者：Aélig Robin、Fraser Brown、Noemí Bahamontes-Rosa、Binghua Wu、Eric Beitz、Jürgen F. J. Kun、Sabine L. Flitsch

  DOI：10.1021/jm070553l

  日期：2007.8.1

  A series of 1-aminopropan-2-ols were synthesized and evaluated against two strains of malaria, Plasmodium falciparum FCR3 (chloroquine-resistant) and 3D7 (chloroquine-sensitive). Microwave-assisted ring opening of epoxides (aryl and alkyl glycidyl ethers, glycidol, epichlorohydrin) with various amines without catalysts generated the desired library of beta-amino alcohols rapidly and efficiently. Most of the compounds showed micromolar potency against malaria, with seven of them having IC50 values between 1 and 10 mu M against both Plasmodium falciparum strains.