2-[3-(1-phenylvinyl)-1,2,5-trioxaspiro[5.5]undec-9-ylidene]propionic acid ethyl ester | 868696-29-1

• 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: 2-[3-(1-phenylvinyl)-1,2,5-trioxaspiro[5.5]undec-9-ylidene]propionic acid ethyl ester
• 英文别名: 2-[3-(1-phenyl-vinyl)-1,2,5-trioxa-spiro[5.5]undec-9-ylidene]-propionic acid ethyl ester；[3-(1-phenyl-vinyl)-1,2,5-trioxa-spiro[5.5]undec-9-ylidene]-propionic acid ethyl ester；Ethyl 2-[3-(1-phenylethenyl)-1,2,5-trioxaspiro[5.5]undecan-9-ylidene]propanoate
• CAS: 868696-29-1
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: IDFGEBVHUDMTDG-UHFFFAOYSA-N

物化性质

• 沸点：
  484.9±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(1-phenylvinyl)-1,2,5-trioxaspiro[5.5]undec-9-ylidene]propionic acid ethyl ester 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到2-(4-氧代环己基)丙酸乙酯
  参考文献：
  名称：

  羰基作为1,2,4-三恶烷的保护及其在碱性条件下的再生。

  摘要：

  [化学反应：见正文]。提出了一个实验方案，证明了羰基作为1,2,4-三恶烷的保护，该保护基在各种反应条件下的稳定性以及在室温下用Triton B在THF中再生羰基的实验方案。该方法为保护具有酸敏感性部分的羰基化合物提供了有用的替代方法。

  DOI：

  10.1021/ol052378d
• 作为产物：
  描述：

  (E)-3-phenylbut-2-en-1-ol 在 盐酸 、 氧气 、 亚甲兰 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 23.5h， 生成 2-[3-(1-phenylvinyl)-1,2,5-trioxaspiro[5.5]undec-9-ylidene]propionic acid ethyl ester
  参考文献：
  名称：

  Orally Active 1,2,4-Trioxanes:  Synthesis and Antimalarial Assessment of a New Series of 9-Functionalized 3-(1-Arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against Multi-Drug-Resistant Plasmodium yoelii nigeriensis in Mice

  摘要：

  Using easily accessible keto-trioxanes 7a-g as the starting materials, a series of new variously functionalized 1,2,4-trioxanes 10-36 have been prepared and evaluated for antimalarial activity against multi-drug-resistant Plasmodium yoelii nigeriensis in mice in the dose range of 24 mg/kg x 4 days to 96 mg/kg x 4 days by oral route. Trioxanes 10, 12, 14, 16, 18, 20, and 22 have shown promising antimalarial activity. Trioxanes 14 and 18, the two most active compounds of the series, provide 100% and 60% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively. In this model beta-arteether provides 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively.

  DOI：

  10.1021/jm051130r

文献信息

• Novel spiro-1,2,4-trioxanes
  申请人：Singh Chandan

  公开号：US20070191475A1

  公开（公告）日：2007-08-16

  The present invention relates to spiro 1,2,4-trioxanes of general formula 4. This invention more particularly relates to a process for the preparation of a series of spiro 1,2,4-trioxanes. Wherein, Ar represents aryl groups such as phenyl, 4-biphenyl, 4-chlorophenyl, 4-methoxyphenyl, 4-methylphenyl, 4-cyclohexylphenyl, 1-naphthyl, 2-naphthyl and the like and R represents hydrogen or the alkyl group such as methyl, ethyl and the like. Several of these compounds show high order of antimalarial activity against multidrug-resistant malaria in mice and thus hold promise as antimalarial agents against multidrug-resistant malaria.

  本发明涉及一般式4的螺环1,2,4-三氧杂环丙烷。该发明更具体地涉及一种制备一系列螺环1,2,4-三氧杂环丙烷的方法。其中，Ar代表芳基团，如苯基、4-联苯基、4-氯苯基、4-甲氧基苯基、4-甲基苯基、4-环己基苯基、1-萘基、2-萘基等，R代表氢或烷基，如甲基、乙基等。这些化合物中的几种显示出高度的抗疟活性，对多药耐药性疟疾在小鼠中具有作用，并因此有望作为抗多药耐药性疟疾的抗疟药物。
• New orally active spiro 1,2,4-trioxanes with high antimalarial potency
  作者：Chandan Singh、Heetika Malik、Sunil K. Puri

  DOI：10.1016/j.bmcl.2005.07.013

  日期：2005.10

  A new series of functionalized 1,2,4-trioxanes 10-21 have been prepared and assessed for antimalarial activity in mice. Several of these trioxanes show significant activity. Trioxane 16, the most active compound of the series, has shown activity by oral route which is comparable with that of the clinically used drug, beta-arteether.

  已经制备了一系列新的官能化的1,2,4-三恶烷类化合物10-21，并评估了其在小鼠中的抗疟活性。这些三恶烷中有几种显示出显着的活性。该系列中最活泼的化合物三恶烷16通过口服途径表现出的活性与临床上使用的药物β-蒿醚相当。
• Orally Active 1,2,4-Trioxanes:  Synthesis and Antimalarial Assessment of a New Series of 9-Functionalized 3-(1-Arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against Multi-Drug-Resistant <i>Plasmodium </i><i>y</i><i>oelii</i> <i>n</i><i>igeriensis</i> in Mice
  作者：Chandan Singh、Heetika Malik、Sunil K. Puri

  DOI：10.1021/jm051130r

  日期：2006.5.1

  Using easily accessible keto-trioxanes 7a-g as the starting materials, a series of new variously functionalized 1,2,4-trioxanes 10-36 have been prepared and evaluated for antimalarial activity against multi-drug-resistant Plasmodium yoelii nigeriensis in mice in the dose range of 24 mg/kg x 4 days to 96 mg/kg x 4 days by oral route. Trioxanes 10, 12, 14, 16, 18, 20, and 22 have shown promising antimalarial activity. Trioxanes 14 and 18, the two most active compounds of the series, provide 100% and 60% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively. In this model beta-arteether provides 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively.
• Protection of the Carbonyl Group as 1,2,4-Trioxane and Its Regeneration under Basic Conditions¹
  作者：Chandan Singh、Heetika Malik

  DOI：10.1021/ol052378d

  日期：2005.12.1

  An experimental protocol demonstrating the protection of the carbonyl group as 1,2,4-trioxane, the stability of the protecting group under a variety of reaction conditions, and the regeneration of the carbonyl group with Triton B in THF at room temperature is presented. The method provides a useful alternative for the protection of carbonyl compounds having acid-sensitive moieties.

  [化学反应：见正文]。提出了一个实验方案，证明了羰基作为1,2,4-三恶烷的保护，该保护基在各种反应条件下的稳定性以及在室温下用Triton B在THF中再生羰基的实验方案。该方法为保护具有酸敏感性部分的羰基化合物提供了有用的替代方法。