(1S,3E,5S)-5-methyl-1-(4-nitrophenyl)-5-phenylhept-3-en-1-ol | 1428538-04-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1S,3E,5S)-5-methyl-1-(4-nitrophenyl)-5-phenylhept-3-en-1-ol
• CAS: 1428538-04-8
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: GYTKYGAVZOOVRV-OBHOAJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (3S,4S)-3-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-4-methyl-4-phenylhex-1-ene 、 对硝基苯甲醛 在 正丁基锂 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以62%的产率得到(1S,3E,5S)-5-methyl-1-(4-nitrophenyl)-5-phenylhept-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