(1S,2Z,5S)-1,5-diphenylpent-2-ene-1,5-diol | 1274953-71-7

• 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: (1S,2Z,5S)-1,5-diphenylpent-2-ene-1,5-diol
• 英文别名: (Z,1S,5S)-1,5-diphenylpent-2-ene-1,5-diol
• CAS: 1274953-71-7
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: GRSHZFAGHKMAPD-YNUCIAJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane 在 potassium dihydrogenphosphate 、 三甲基氯硅烷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (2Z)-1,5-diphenylpent-2-ene-1,5-diol 、 (1S,2Z,5S)-1,5-diphenylpent-2-ene-1,5-diol
  参考文献：
  名称：

  Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin

  摘要：

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.

  DOI：

  10.1021/ol2003836

文献信息

• Enantio- and Diastereoselective Synthesis of (<i>E</i>)-1,5-<i>syn</i>-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin
  作者：Jeremy Kister、Philippe Nuhant、Ricardo Lira、Achim Sorg、William R. Roush

  DOI：10.1021/ol2003836

  日期：2011.4.1

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.