rac-ethyl 2,8-dimethylchroman-2-carboxylate | 1433065-38-3

• 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: rac-ethyl 2,8-dimethylchroman-2-carboxylate
• 英文别名: Ethyl 2,8-dimethyl-3,4-dihydrochromene-2-carboxylate；ethyl 2,8-dimethyl-3,4-dihydrochromene-2-carboxylate
• CAS: 1433065-38-3
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: DEFLHOWEROYGGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-羟基-3-甲基苯甲醛 在 咪唑 、 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 potassium tert-butylate 、 水 、 碘 、 双(三甲基硅烷基)氨基钾 、 三苯基膦 、 copper dichloride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 rac-ethyl 2,8-dimethylchroman-2-carboxylate 、 ethyl 2-(2’-methyl-6’-vinylphenoxy)propanoate
  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.