Propanoic acid, 2-(ethenyloxy)-, ethyl ester, (S)- | 149070-68-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Propanoic acid, 2-(ethenyloxy)-, ethyl ester, (S)-
• 英文别名: (-)-2-vinyloxypropionate d'ethyle；ethyl (S)-2-(vinyloxy)propanate
• CAS: 149070-68-8
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: WGXWUGDWENWDAT-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-氧代-4-苯基-3-丁酸甲酯 、 Propanoic acid, 2-(ethenyloxy)-, ethyl ester, (S)- 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium 作用下， 以 正己烷 为溶剂， 反应 108.0h， 生成
  参考文献：
  名称：

  Synthèse asymétrique et configuration absolue de dihydropyranes substitués, par hétérocycloaddition intermoléculaire d'éthers vinyliques chiraux

  摘要：

  The alkyl vinyl ethers 2b-8b (deriving from the alcohols 2a-8a) smoothly reacted with methyl E-benzylidenepyruvate 10 in the presence of catalytic amounts of Eu(fod)(3) or Yb(fod)(3) in refluxing hexane, thus leading to the dihydropyran endo adducts 13-19 in high yields (80-95%). The endo-cycloadducts 13-17 were obtained with diastereofacial selectivities (ds) ranging from 76/24 to 87.5/12.5. Asymmetric induction was found to culminate with the vinyl ether (-)-7b deriving from n-butyl (R)-(-)-mandelate : the best ds (92.5/7.5) was obtained for the corresponding adduct 18 after 6 days at room temperature. The absolute configurations of the major isomers of the dihydropyrans 16-18, 20 and 21 were established by oxydative degradation to optically active alpha-phenylsuccinic acid derivatives.

  DOI：

  10.1016/s0040-4020(01)85370-9
• 作为产物：
  描述：

  L(-)-乳酸乙酯 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 113.0h， 生成 Propanoic acid, 2-(ethenyloxy)-, ethyl ester, (S)-
  参考文献：
  名称：

  高效无水制备手性仲醇和α-羟基酯的乙烯基和异丙烯基醚

  摘要：

  易于从α-手性醇1a-h和乙基乙烯基醚或异丙烯基甲基醚衍生而来的混合缩醛2a-h和5a-d，在用三乙胺和三甲基甲硅烷基三氟甲磺酸酯处理后，选择性地除去了伯醇，因此得到了良好的高分别得到手性烯醇醚3a-h和6a-d的产率。

  DOI：

  10.1016/0040-4039(95)00087-s

文献信息

• Asymmetric Synthesis of 2,3-Dihydro-4-pyranones by Reaction of Chiral 3-Alkoxycyclobutanone and Aldehydes
  作者：Shoko Negishi、Hiroyuki Ishibashi、Jun-ichi Matsuo

  DOI：10.1021/ol1021355

  日期：2010.11.5

  Chiral cyclobutanone which had ethyl L-lactate as a chiral auxiliary at the 3-position reacted with aldehydes to give 2,3-dihydro-4-pyranones in up to 93% ee by combined use of titanium(IV) chloride and tin(II) chloride.
• Asymmetric syntheses of substituted dehydropyrans by Diels-Alder heterocycloadditions involving chiral vinyl ethers as dienophiles
  作者：Gillea Dujardin、Samira Molato、Bric Brown

  DOI：10.1016/s0957-4166(00)82335-6

  日期：1993.2

  The alkyl vinyl ethers 2b-8b (deriving from the alcohols 2a-8a) smoothly reacted with methyl E-benzylidenepyruvate 1 in the presence of catalytic amounts of Eu(fod)3, thus leading to the endo cycloadducts 9-15 in high yields. The cycloadducts 12-15 were obtained with moderate to good diastereomeric excesses (43-72%). Thus the vinyl ether Bb deriving from methyl (R)-mandelate gave the endo adduct IS in 83% yield and with 72% diastereomeric excess.