(S)-4-isopropyl-3-((S)-2-methyloctanoyl)oxazolidin-2-one | 1415133-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-4-isopropyl-3-((S)-2-methyloctanoyl)oxazolidin-2-one
• 英文别名: (4S)-3-[(2S)-2-methyloctanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1415133-43-5
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: RYLONMHMJLDHKA-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-3-((S)-2-methyloctanoyl)oxazolidin-2-one 在 甲醇 、 锂硼氢 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以93%的产率得到(2S)-2-methyloctan-1-ol
  参考文献：
  名称：

  Efficient asymmetric synthesis of long chain methyl-branched hydrocarbons, components of the contact sex pheromone of females of the cerambycid beetle, Neoclytus acuminatus acuminatus

  摘要：

  Both enantiomers of 7-methylheptacosane and 7-methylpentacosane, the major components of the female-produced contact sex pheromone of the red-headed ash borer beetle (Neoclytus acuminatus accuminatus) were synthesized in 62-68% overall yield (six steps) via alkynylation of the triflate of a shared chiral alcohol intermediate (R)- or (S)-2-methyloctanol. The enantiomers of the shared intermediate were prepared via acylation and subsequent asymmetic methylation of (R)- and (S)-4-isopropyloxazolidin-2-one chiral auxiliaries, respectively. The methodology can be readily adapted for the preparation of analogues with any desired chain length and methyl branch positions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.021
• 作为产物：
  描述：

  (S)-4-异丙基-2-唑烷酮 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.16h， 生成 (S)-4-isopropyl-3-((S)-2-methyloctanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Efficient asymmetric synthesis of long chain methyl-branched hydrocarbons, components of the contact sex pheromone of females of the cerambycid beetle, Neoclytus acuminatus acuminatus

  摘要：

  Both enantiomers of 7-methylheptacosane and 7-methylpentacosane, the major components of the female-produced contact sex pheromone of the red-headed ash borer beetle (Neoclytus acuminatus accuminatus) were synthesized in 62-68% overall yield (six steps) via alkynylation of the triflate of a shared chiral alcohol intermediate (R)- or (S)-2-methyloctanol. The enantiomers of the shared intermediate were prepared via acylation and subsequent asymmetic methylation of (R)- and (S)-4-isopropyloxazolidin-2-one chiral auxiliaries, respectively. The methodology can be readily adapted for the preparation of analogues with any desired chain length and methyl branch positions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.021

文献信息

• A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal
  作者：Xun Liu、T. Maxwell Deaton、Fredrik Haeffner、James P. Morken

  DOI：10.1002/anie.201705720

  日期：2017.9.11

  unusual net [2+2] cycloaddition reaction between boron alkylidenes and unactivated alkenes. This reaction provides a new method for the construction of carbocyclic ring systems bearing versatile organoboronic esters. Aside from surveying the scope of this reaction, we provide details about the mechanistic underpinnings of this process, and examine its application to the synthesis of the natural product

  我们描述了亚烷基硼和未活化的烯烃之间不寻常的净[2+2]环加成反应。该反应为构建具有多功能有机硼酸酯的碳环系统提供了一种新方法。除了调查该反应的范围之外，我们还提供了有关该过程的机械基础的详细信息，并检查了其在天然产物 aphanamal 合成中的应用。
• Efficient asymmetric synthesis of long chain methyl-branched hydrocarbons, components of the contact sex pheromone of females of the cerambycid beetle, Neoclytus acuminatus acuminatus
  作者：Jan E. Bello、Jocelyn G. Millar

  DOI：10.1016/j.tetasy.2013.05.021

  日期：2013.7

  Both enantiomers of 7-methylheptacosane and 7-methylpentacosane, the major components of the female-produced contact sex pheromone of the red-headed ash borer beetle (Neoclytus acuminatus accuminatus) were synthesized in 62-68% overall yield (six steps) via alkynylation of the triflate of a shared chiral alcohol intermediate (R)- or (S)-2-methyloctanol. The enantiomers of the shared intermediate were prepared via acylation and subsequent asymmetic methylation of (R)- and (S)-4-isopropyloxazolidin-2-one chiral auxiliaries, respectively. The methodology can be readily adapted for the preparation of analogues with any desired chain length and methyl branch positions. (C) 2013 Elsevier Ltd. All rights reserved.