ethyl (E)-2-hydroxynon-3-enoate | 187950-65-8

• 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: ethyl (E)-2-hydroxynon-3-enoate
• CAS: 187950-65-8
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: BJLNVVUKNKXOKY-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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 (E)-2-hydroxynon-3-enoate 在 lithium aluminium tetrahydride 、 diethylzinc 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S)-1-((1R,2R)-2-Pentyl-cyclopropyl)-ethane-1,2-diol
  参考文献：
  名称：

  手性环丙基甲基硅烷的汞-脱甲硅烷基化研究 - 一种立体控制的 Carba 糖

  摘要：

  环丙基甲基硅烷的汞去甲硅烷基化提供了对均烯丙基汞中间体的立体有择访问，可以进一步详细说明。该策略通过对carba-呋喃糖和carba-C-二糖的短暂访问来说明。

  DOI：

  10.1002/(sici)1099-0690(200002)2000:3<401::aid-ejoc401>3.0.co;2-m
• 作为产物：
  描述：

  ethyl (E)-2-diazonon-3-enoate 在 dirhodium tetraacetate 、 水 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以53%的产率得到ethyl (E)-2-hydroxynon-3-enoate
  参考文献：
  名称：

  A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds

  摘要：

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.

  DOI：

  10.1021/jo961952j

文献信息

• A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds
  作者：Priyadarshanie Bulugahapitiya、Yannick Landais、Liliana Parra-Rapado、Denis Planchenault、Valéry Weber

  DOI：10.1021/jo961952j

  日期：1997.3.1

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
• Studies on the Mercury-Desilylation of Chiral Cyclopropylmethylsilanes - A Stereocontrolled Access to Carba-Sugars
  作者：Yannick Landais、Liliana Parra-Rapado

  DOI：10.1002/(sici)1099-0690(200002)2000:3<401::aid-ejoc401>3.0.co;2-m

  日期：2000.2

  Mercury-desilylation of cyclopropylmethylsilanes affords a stereospecific access to homoallylic mercury intermediates, which can be elaborated further. This strategy is illustrated with a short access to carba-furanoses and carba-C-disaccharides.

  环丙基甲基硅烷的汞去甲硅烷基化提供了对均烯丙基汞中间体的立体有择访问，可以进一步详细说明。该策略通过对carba-呋喃糖和carba-C-二糖的短暂访问来说明。