3-hydroperoxy-4-(1-naphthyl)pent-4-en-1-ol | 917100-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroperoxy-4-(1-naphthyl)pent-4-en-1-ol
• 英文别名: 3-Hydroperoxy-4-naphthalen-1-ylpent-4-en-1-ol
• CAS: 917100-92-6
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: MBJAYDAUCLCHLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroperoxy-4-(1-naphthyl)pent-4-en-1-ol 、 丙酮 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到7-[1-(1-naphthyl)vinyl]-3,3-dimethyl-[1,2,4]-trioxepane
  参考文献：
  名称：

  Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹

  摘要：

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

  DOI：

  10.1021/jo061414z
• 作为产物：
  描述：

  4-(1-naphthyl)pent-3-en-1-ol 在 氧气 、 亚甲兰 作用下， 以 乙腈 为溶剂， 反应 27.0h， 以68%的产率得到3-hydroperoxy-4-(1-naphthyl)pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹

  摘要：

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

  DOI：

  10.1021/jo061414z

文献信息

• Orally active 1,2,4-trioxepanes: Synthesis and antimalarial activity of a series of 7-arylvinyl-1,2,4-trioxepanes against multidrug-resistant Plasmodium yoelii in Swiss mice☆
  作者：Chandan Singh、Shilpi Pandey、Malvika Sharma、Sunil K. Puri

  DOI：10.1016/j.bmc.2007.11.012

  日期：2008.2.15

  7-Arylvinyl-1,2,4-trioxepanes 7a-d, 8a-d, 9a-d, 10a-d, 11a-c, and 12a-c, prepared by photooxygenation of homoallylic alcohols 5a-d, were evaluated against multi-drug resistant Plasmodium yoelii nigeriensis in Swiss mice by oral and intramuscular routes. Trioxepane 11c, the most active compound of the series, showed more than 98% suppression of parsitaemia at 96 mg/kg by both oral and intramuscular routes. This is the first report on in vivo active 1,2,4-trioxepanes. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹
  作者：Chandan Singh、Shilpi Pandey、Gunjan Saxena、Nisha Srivastava、Malvika Sharma

  DOI：10.1021/jo061414z

  日期：2006.11.1

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.