(1S,3E)-1,6-diphenylhex-3-en-1-ol | 1428537-73-8

• 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,3E)-1,6-diphenylhex-3-en-1-ol
• 英文别名: (E,1S)-1,6-diphenylhex-3-en-1-ol
• CAS: 1428537-73-8
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: FLBVXROHYNSVKD-UHIOCVRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,3E)-1,6-diphenylhex-3-en-1-ol 在 氧气 、 臭氧 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.0h， 以9%的产率得到(S)-1-苯基-1,3-丙二醇
  参考文献：
  名称：

  Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α-Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters

  摘要：

  Readily available, alpha-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with TFAA leads to an intermediate allyl borinic ester which undergoes allylboration with very high E selectivity. The substrate scope includes primary to tertiary alkyl alpha-substituents, crotyl substrates, and the previously unreported beta-methallyl pinacol boronic esters. The latter give very high Z selectivity under standard conditions which is completely reversed to high E selectivity under the new conditions. Monitoring the reaction by B-11 NMR confirmed that the reaction proceeds through a borinic ester intermediate.

  DOI：

  10.1021/ja401564z
• 作为产物：
  描述：

  苯丙氨酯 在 正丁基锂 、 (2-methylpropyl)lithium 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 22.75h， 生成 (1S,3E)-1,6-diphenylhex-3-en-1-ol
  参考文献：
  名称：

  Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α-Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters

  摘要：

  Readily available, alpha-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with TFAA leads to an intermediate allyl borinic ester which undergoes allylboration with very high E selectivity. The substrate scope includes primary to tertiary alkyl alpha-substituents, crotyl substrates, and the previously unreported beta-methallyl pinacol boronic esters. The latter give very high Z selectivity under standard conditions which is completely reversed to high E selectivity under the new conditions. Monitoring the reaction by B-11 NMR confirmed that the reaction proceeds through a borinic ester intermediate.

  DOI：

  10.1021/ja401564z

文献信息

• Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α-Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters
  作者：Jack L.-Y. Chen、Helen K. Scott、Matthew J. Hesse、Christine L. Willis、Varinder K. Aggarwal

  DOI：10.1021/ja401564z

  日期：2013.4.10

  Readily available, alpha-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with TFAA leads to an intermediate allyl borinic ester which undergoes allylboration with very high E selectivity. The substrate scope includes primary to tertiary alkyl alpha-substituents, crotyl substrates, and the previously unreported beta-methallyl pinacol boronic esters. The latter give very high Z selectivity under standard conditions which is completely reversed to high E selectivity under the new conditions. Monitoring the reaction by B-11 NMR confirmed that the reaction proceeds through a borinic ester intermediate.