n-butyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate | 1143580-36-2

• 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: n-butyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate
• 英文别名: butyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate
• CAS: 1143580-36-2
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: YTYZUMSBJJXCMX-UHFFFAOYSA-N

物化性质

• 沸点：
  315.5±31.0 °C(predicted)
• 密度：
  0.942±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  n-butyl 2-hydroxy-3-(trimethylsilyl)penta-3,4-dienoate 、 特戊醛 在 indium(III) triflate 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(2,6-trans)-butyl 4-bromo-6-tert-butyl-3-(trimethylsilyl)-5,6-dihydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Stereoelectronic versus Steric Tuning in the Prins Cyclization Reaction: Synthesis of 2,6-trans Pyranyl Motifs

  摘要：

  The use of carboalkoxyl allenic alcohol for the efficient synthesis of pyranyl motifs via Prins cyclization is described. This method provides easy access to 2,6-trans dihydropyrans in good yield and high diastereoselectivity.

  DOI：

  10.1021/ol900196w
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 乙醛酸正丁酯 在 indium 、 水 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到n-butyl 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.
• Stereoelectronic versus Steric Tuning in the Prins Cyclization Reaction: Synthesis of 2,6-<i>trans</i> Pyranyl Motifs
  作者：Xu-Hong Hu、Feng Liu、Teck-Peng Loh

  DOI：10.1021/ol900196w

  日期：2009.4.16

  The use of carboalkoxyl allenic alcohol for the efficient synthesis of pyranyl motifs via Prins cyclization is described. This method provides easy access to 2,6-trans dihydropyrans in good yield and high diastereoselectivity.