(Z,2R)-2-methyl-4-phenylmethoxybut-3-enoic acid | 1393834-14-4

• 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: (Z,2R)-2-methyl-4-phenylmethoxybut-3-enoic acid
• CAS: 1393834-14-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: JLYRSVTUXFORLI-GQYWMQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (Z,2R)-2-methyl-4-phenylmethoxybut-3-enoic acid 反应 72.0h， 生成
  参考文献：
  名称：

  ‘Syn-effect’ in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

  摘要：

  Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in alpha, beta-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the gamma-substituent in the alpha, beta-unsaturated carbonyl. This stereo-selectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.037
• 作为产物：
  描述：

  在 双氧水 、 双(三甲基硅烷基)氨基钾 、 lithium chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.8h， 生成 (Z,2R)-2-methyl-4-phenylmethoxybut-3-enoic acid
  参考文献：
  名称：

  Diastereoselective alkylations of oxazolidinone vinylogous glycolates

  摘要：

  A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the gamma-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.133