3-(4-bromophenyl)-2-hydroperoxybut-3-en-1-ol | 948049-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-bromophenyl)-2-hydroperoxybut-3-en-1-ol
• CAS: 948049-20-5
• 化学式: C₁₀H₁₁BrO₃
• 分子量: 259.1
• InChiKey: QYQZPRUBTQJHRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-2-hydroperoxybut-3-en-1-ol 、 methyl 8-sec-butyl-6-formyl-2-oxo-2H-chromene-3-carboxylate 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 methyl 6-(6-(1-(4-bromophenyl)vinyl)-1,2,4-trioxan-3-yl)-8-sec-butyl-2-oxo-2H-chromene-3-carboxylate
  参考文献：
  名称：

  香豆素-三恶烷杂化物：合成和评估作为一类新的抗疟疾支架

  摘要：

  据报道，首次合成了新型香豆素-三恶烷杂化物。在对甲苯磺酸的存在下，通过β-羟基氢过氧化物与香豆醛-醛的缩合可实现高收率，并在体外和体内评估了新型杂种的抗疟活性。

  DOI：

  10.1016/j.bmcl.2012.04.100
• 作为产物：
  描述：

  (E)-3-(4-bromophenyl)but-2-en-1-ol 在 氧气 、 亚甲兰 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 3-(4-bromophenyl)-2-hydroperoxybut-3-en-1-ol
  参考文献：
  名称：

  Orally active antimalarials: Synthesis and bioevaluation of a new series of steroid-based 1,2,4-trioxanes against multi-drug resistant malaria in mice

  摘要：

  A new series of steroid-based 1,2,4-trioxanes 7a-f, 8a-f and 9b-e have been synthesized and evaluated for their antimalarial activity against multi-drug resistant Plasmodium yoelii in Swiss mice by oral route. The biological activity shows a strong dependence on the size and the nature of the steroidal side chain. Pregnane-based trioxanes 8a-f show better activity profile than trioxanes 7a-f and 9b-e, derived from cholesterol and tigogenine, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.055

文献信息

• Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment
  作者：Chandan Singh、Mohammad Hassam、Ved Prakash Verma、Ajit Shanker Singh、Niraj Krishna Naikade、Sunil K. Puri、Prakas R. Maulik、Ruchir Kant

  DOI：10.1021/jm301323k

  日期：2012.12.13

  A new series of bile acid-based trioxanes 23a-d, 24a-d, 25a-d, 26a, 26b, and 26d have been synthesized and assessed for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. The antimalarial activity of these trioxanes showed a strong dependence on the side-chain length; shortening side-chain length lead to increase in activity. The antimalarial activity also showed even stronger dependence on the stereochemistry at C3 and C6 (C21 in Figure 5) of the trioxane moiety. Of the two diastereomers isolated of each of the trioxanes, more polar one was significantly more active than the less polar one. The more polar diastereomer of the trioxanes 26a, 26b, and 26d, were the most active compounds of the series. All these three trioxanes provided 100% protection at 24 mg/kg X 4 days. In this model beta-arteether provided 100% and 20% protection at 48 mg/kg X 4 days and 24 mg/kg X 4 days, respectively.