2-bromoethyl 5-(5-methyl-5-methoxycarbonyl-[1,2,4]trioxolan-3-yl)-pentanoate

• 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: 2-bromoethyl 5-(5-methyl-5-methoxycarbonyl-[1,2,4]trioxolan-3-yl)-pentanoate
• 英文别名: Methyl 5-[5-(2-bromoethoxy)-5-oxopentyl]-3-methyl-1,2,4-trioxolane-3-carboxylate
• 化学式: C₁₂H₁₉BrO₇
• 分子量: 355.183
• InChiKey: WYQGBEZZJIJXKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(5-methyl-5-methoxycarbonyl-[1,2,4]trioxolan-3-yl)-pentanal 1,3-dioxolane 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到2-bromoethyl 5-(5-methyl-5-methoxycarbonyl-[1,2,4]trioxolan-3-yl)-pentanoate
  参考文献：
  名称：

  Chemoselective reactions of a compound containing both aldehyde and ozonide groups

  摘要：

  The aldehyde of compound 2 is more reactive than the ozonide in the carbon-carbon bond formation reactions. The ozonide is stable under the Lewis acid, radical and organometallic conditions where aldehyde reacts efficiently. The ozonide moiety can be considered as a synthon or protecting group for the aldehyde and carboxylic acid.

  DOI：

  10.1016/0040-4039(94)88334-3

文献信息

• Chemoselective reaction on a hydroxy or aldehyde group tethered with a tri-substituted ozonide: A versatile methodology for the preparation of terminally differentiated compounds from cyclohexene
  作者：Yung-Son Hon、Jiann-Long Yan

  DOI：10.1016/s0040-4020(98)00452-9

  日期：1998.7

  Molecules containing a hydroxy or aldehyde group tethered with a tri-substituted ozonide moiety were prepared. We have demonstrated that the ozonide group is stable under certain Lewis acidic, free radical, and organometallic conditions. Therefore, chemoselective elaboration of the hydroxy or aldehyde group is possible under these conditions. These functional group transformations followed by the decomposition

  制备了含有羟基或醛基与三取代的臭氧化物部分相连的分子。我们已经证明，臭氧化物基团在某些路易斯酸性，自由基和有机金属条件下是稳定的。因此，在这些条件下可以对羟基或醛基进行化学选择性修饰。这些官能团的转化以及随后的臭氧化物部分的分解为从对称环己烯制备最终分化的化合物提供了极为方便且通用的方法。
• Hon Yung-Son, Yan Jiann-Long, Tetrahedron Lett, 35 (1994) N 11, S 1743-1746
  作者：Hon Yung-Son, Yan Jiann-Long

  DOI：——

  日期：——
• Chemoselective reactions of a compound containing both aldehyde and ozonide groups
  作者：Yung-Son Hon、Jiann-Long Yan

  DOI：10.1016/0040-4039(94)88334-3

  日期：1994.3

  The aldehyde of compound 2 is more reactive than the ozonide in the carbon-carbon bond formation reactions. The ozonide is stable under the Lewis acid, radical and organometallic conditions where aldehyde reacts efficiently. The ozonide moiety can be considered as a synthon or protecting group for the aldehyde and carboxylic acid.