9-[1-(4-Chlorophenyl)ethenyl]-7,8,12-trioxaspiro[5.6]dodecan-3-one | 1019360-71-4

• 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: 9-[1-(4-Chlorophenyl)ethenyl]-7,8,12-trioxaspiro[5.6]dodecan-3-one
• CAS: 1019360-71-4
• 化学式: C₁₇H₁₉ClO₄
• 分子量: 322.788
• InChiKey: VLJPXGKKCOMHET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[1-(4-Chlorophenyl)ethenyl]-7,8,12-trioxaspiro[5.6]dodecan-3-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以77%的产率得到9-[1-(4-Chlorophenyl)ethenyl]-7,8,12-trioxaspiro[5.6]dodecan-3-ol
  参考文献：
  名称：

  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☆

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.11.012
• 作为产物：
  描述：

  4-(4-chlorophenyl)-3-hydroperoxypent-4-en-1-ol 、 1,4-环己二酮 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以43%的产率得到9-[1-(4-Chlorophenyl)ethenyl]-7,8,12-trioxaspiro[5.6]dodecan-3-one
  参考文献：
  名称：

  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☆

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.11.012

文献信息

• New functionalized 1,2,4-trioxepanes: Synthesis and antimalarial activity against multi-drug resistant P. yoelii in mice
  作者：Chandan Singh、Shilpi Pandey、Ambuj K. Kushwaha、Sunil K. Puri

  DOI：10.1016/j.bmcl.2008.08.096

  日期：2008.10

  A series of new amino functionalized 1,2,4-trioxepanes8-16 and ester functionalized 1,2,4-trioxepanes 17-19 have been synthesized and evaluated against multi-drug resistant Plasmodium yoelii in Swiss mice. Amino functionalized trioxepanes 14, the most active compound of the series, showed 100% clearance of parasitaemia by oral route on day 4 and 75% protection to the treated mice beyond day 28. (C) 2008 Elsevier Ltd. All rights reserved.