ethyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate | 1215863-60-7

• 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 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate
• CAS: 1215863-60-7
• 化学式: C₁₀H₁₈O₃Si
• 分子量: 214.337
• InChiKey: UPPVRMNTGVAFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate 、 环己烷基甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 ethyl (2,6-cis)-6-cyclohexyl-4-fluoro-3-(trimethylsilyl)-5,6-dihydro-2H-pyran-2-carboxylate 、 ethyl (2,6-trans)-6-cyclohexyl-4-fluoro-3-(trimethylsilyl)-5,6-dihydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

  摘要：

  A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3 center dot Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.068
• 作为产物：
  描述：

  乙醛酸乙酯 、 3-溴-1-三甲基硅基-1-丙炔 在 indium 、 水 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到ethyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate
  参考文献：
  名称：

  Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

  摘要：

  A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3 center dot Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.068

文献信息

• Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization
  作者：Hai-Qing Luo、Xu-Hong Hu、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2009.12.068

  日期：2010.2

  A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3 center dot Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities. (C) 2010 Elsevier Ltd. All rights reserved.