(S)-ethyl 2-hydroxy-4-p-tolylpent-4-enoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-ethyl 2-hydroxy-4-p-tolylpent-4-enoate
• 英文别名: ethyl (S)-2-hydroxy-4-p-tolylpent-4-enoate；ethyl (2S)-2-hydroxy-4-(4-methylphenyl)pent-4-enoate
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: RJRIACWKFLXMIF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-ethyl 2-hydroxy-4-p-tolylpent-4-enoate 、 丙醛 在 iron(III) chloride 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

  摘要：

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.

  DOI：

  10.1021/ja3062002
• 作为产物：
  描述：

  乙醛酸乙酯 、 1-甲基-4-(1-甲基乙烯基)苯 在 2,6-二叔丁基吡啶 、 [Rh₂(S,S-MenPY)₄]SbF₆ 作用下， 以 neat (no solvent) 为溶剂， 反应 72.0h， 以94%的产率得到(S)-ethyl 2-hydroxy-4-p-tolylpent-4-enoate
  参考文献：
  名称：

  手性阳离子氨基甲酸吡啶二酯（II，III）催化对映选择性羰基-烯反应

  摘要：

  本文描述了乙醛酸酯与手性阳离子氨基羧酸二氨基（II，III）催化的乙醛酸酯与1,1-二取代烯烃的对映选择性羰基-烯反应。在每个铑上具有一个开放配位位的氨基甲酸二（II，III）氨基甲酸酯能平稳地催化羰基-烯反应，以高分离度和良好的对映选择性提供均相醇产物。

  DOI：

  10.1021/jo5013674

文献信息

• Significant counterion effect of the In(III)–pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate
  作者：Jun-Feng Zhao、Teguh-Budiono W. Tjan、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2010.06.066

  日期：2010.10

  A highly efficient enantioselective carbonyl-ene reaction of ethyl glyoxylate catalyzed by an In(III)-pybox complex, which is designed based on the counterion effect, is reported. Reactions of both aliphatic and aromatic 1,1-disubstituted olefins proceed smoothly to give enantioenriched homoallylic alcohols with excellent yields and enantioselectivities. In addition, electron-withdrawing as well as donating groups on the phenyl ring of alpha-methyl styrenes are tolerated in this reaction. (C) 2010 Elsevier Ltd. All rights reserved.