ethyl 3-(tert-butyldimethylsilyloxy)-5-methylhex-4-enoate | 1158439-80-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(tert-butyldimethylsilyloxy)-5-methylhex-4-enoate
• CAS: 1158439-80-5
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: UXHNPTNKHFBHFK-UHFFFAOYSA-N

物化性质

• 沸点：
  297.2±20.0 °C(predicted)
• 密度：
  0.907±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(tert-butyldimethylsilyloxy)-5-methylhex-4-enoate 在 二异丁基氢化铝 、 sodium tetrahydroborate 作用下， 以 正己烷 、 二氯甲烷 、 甲醇 为溶剂， 反应 3.0h， 以61%的产率得到3-(tert-butyldimethylsilyloxy)-5-methylhex-4-ene-1-ol
  参考文献：
  名称：

  Antimalarial Peroxide Dyads from Natural Artemisinin and Hydroxyalkylated 1,2,4-Trioxanes

  摘要：

  Three synthetic approaches to highly antimalarial peroxide dyads that are composed of the natural artemisinin part (either as dihydroartemisinin or artesunic acid components) and synthetic 1,2,4-trioxanes linked by ether or ester bridges are described. Photooxygenation is the key step to introduce the trioxane group initially or at the end of the reaction sequence, respectively. Dihydroartemisinin or artesunate coupling to hydroxyethyltrioxanes are the two processes that use intact peroxide units from the beginning, whereas the dihydroartemisinin-coupling to an allylic alcohol is a postphotooxygenation route, where the second trioxane ring is installed in the last step of the procedure.

  DOI：

  10.1021/jm9002523
• 作为产物：
  描述：

  ethyl 3-hydroxy-5-methylhex-4-enoate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到ethyl 3-(tert-butyldimethylsilyloxy)-5-methylhex-4-enoate
  参考文献：
  名称：

  Antimalarial Peroxide Dyads from Natural Artemisinin and Hydroxyalkylated 1,2,4-Trioxanes

  摘要：

  Three synthetic approaches to highly antimalarial peroxide dyads that are composed of the natural artemisinin part (either as dihydroartemisinin or artesunic acid components) and synthetic 1,2,4-trioxanes linked by ether or ester bridges are described. Photooxygenation is the key step to introduce the trioxane group initially or at the end of the reaction sequence, respectively. Dihydroartemisinin or artesunate coupling to hydroxyethyltrioxanes are the two processes that use intact peroxide units from the beginning, whereas the dihydroartemisinin-coupling to an allylic alcohol is a postphotooxygenation route, where the second trioxane ring is installed in the last step of the procedure.

  DOI：

  10.1021/jm9002523

文献信息

• Metal-Free, Aerobic Dioxygenation of Alkenes Using Hydroxamic Acids
  作者：Valerie A. Schmidt、Erik J. Alexanian

  DOI：10.1002/anie.201000843

  日期：2010.6.14

  One dioxygenation please, hold the metal: In the presence of either oxygen or air as the sole oxidant and external oxygen atom source, a variety of unsaturated hydroxamic acids afford cyclic hydroxamates that are readily converted into 1,2‐diols, with the potential for high levels of reaction stereocontrol.

  请进行一次双氧合，以固定金属：在氧气或空气作为唯一氧化剂和外部氧原子源的情况下，各种不饱和异羟肟酸提供的环状异羟肟酸酯很容易转化为1,2-二醇，并有可能高水平的反应立体控制。