2-Hydroxyethyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate | 1334832-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Hydroxyethyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate
• CAS: 1334832-05-1
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: YDIFTELBSOWOIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲醛 、 丙烯酸羟乙酯 在 三乙烯二胺 作用下， 以 乙二醇 为溶剂， 反应 144.0h， 以67%的产率得到2-Hydroxyethyl 2-[hydroxy(naphthalen-2-yl)methyl]prop-2-enoate
  参考文献：
  名称：

  Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita–Baylis–Hillman adducts

  摘要：

  We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC50), cytotoxicity assays in macrophages (CC50), and selectivity index (SI=-CC50/IC50) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the "one pot" Morita-Baylis-Hillman Reaction between the aldehydes 29-36 and the acrylates 27 or 28 under DABCO as promoter. The MBHA 2-[Hydroxy(2-nitrophenyl)propyl] propanoate (1, IC50 = 7.52 mu g/mL or 28.38 mu M; CC50 = 35.77 mu g/mL or 134.98 mu M; SI = 4.75) and 2-[Hydroxy(2-[nitrophenyl)hydroxyethyl] propanoate (9, IC50 = 5.48 mu g/mL or 20.52 mu M; CC50 = 29.81 mu g/mL or 111.64c mu M and, SI = 5.43) were the most effective and safe evaluated compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.036