ethyl (2E,4R)-4-hydroxy-2-hexenoate | 148969-13-5

• 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: ethyl (2E,4R)-4-hydroxy-2-hexenoate
• 英文别名: ethyl (E,4R)-4-hydroxyhex-2-enoate
• CAS: 148969-13-5
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: PLKJBIKBHWNOFH-WEWAHIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  ethyl (2E,4R)-4-hydroxy-2-hexenoate 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2E,4R)-4-(tetrahydropyran-2-yloxy)-2-hexenol
  参考文献：
  名称：

  Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents

  摘要：

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00436-1
• 作为产物：
  描述：

  ethyl (4S)-3-hydroxy-4-phenylselanylhexanoate 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以73%的产率得到ethyl (2E,4R)-4-hydroxy-2-hexenoate
  参考文献：
  名称：

  γ-羟基-(E)-α,β-不饱和砜和酯的不对称有机催化三步合成。

  摘要：

  据报道，通过对映体富集的 α-硒醛与 EWG 稳定的碳负离子反应，然后进行一锅硒化物氧化，原位环氧化物形成，最后生成原位环氧化物开环。

  DOI：

  10.1021/ol8020513

文献信息

• Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers
  作者：Benjamin W. Gung、Mark A. Wolf

  DOI：10.1021/jo00077a023

  日期：1993.12

  A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the gamma-hydroxy-alpha,beta-unsaturated esters, which normally favor the CO-eclipsed form (II). On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the gamma-hydroxy-alpha,beta-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes. These facts are explained by the size of the allylic oxygen lone pairs.
• Asymmetric, Organocatalytic, Three-Step Synthesis of γ-Hydroxy-(<i>E</i>)-α,β-Unsaturated Sulfones and Esters
  作者：Kimberly S. Petersen、Gary H. Posner

  DOI：10.1021/ol8020513

  日期：2008.10.16

  Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched alpha-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening.

  据报道，通过对映体富集的 α-硒醛与 EWG 稳定的碳负离子反应，然后进行一锅硒化物氧化，原位环氧化物形成，最后生成原位环氧化物开环。
• Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents
  作者：Hidetaka Nagatomo、Yoh-ichi Matsushita、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.1016/s0957-4166(03)00436-1

  日期：2003.8

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.