ethyl (2R)-8-isopropyl-2,5-dimethylchroman-2-carboxylate | 1433065-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl (2R)-8-isopropyl-2,5-dimethylchroman-2-carboxylate
• 英文别名: ethyl (2R)-2,5-dimethyl-8-propan-2-yl-3,4-dihydrochromene-2-carboxylate
• CAS: 1433065-80-5
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: KCFFCEPRFPQJAA-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (R)-2-(6-isopropyl-2-(2-methoxyvinyl)-3-methylphenoxy)propanoate 在 咪唑 、 sodium tetrahydroborate 、 水 、 碘 、 三苯基膦 、 copper dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 ethyl (2R)-8-isopropyl-2,5-dimethylchroman-2-carboxylate 、 ethyl (2S)-8-isopropyl-2,5-dimethylchroman-2-carboxylate
  参考文献：
  名称：

  Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis

  摘要：

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.

  DOI：

  10.1021/ja4018122

文献信息

• Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis
  作者：Tomoyuki Yoshimura、Keisuke Tomohara、Takeo Kawabata

  DOI：10.1021/ja4018122

  日期：2013.5.15

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.