(2R)-ethyl 2-[2’-(2’’-iodoethyl)phenoxy]propanoate | 1433064-57-3

• 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: (2R)-ethyl 2-[2’-(2’’-iodoethyl)phenoxy]propanoate
• CAS: 1433064-57-3
• 化学式: C₁₃H₁₇IO₃
• 分子量: 348.181
• InChiKey: BLLCQIWAEIJSKW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (2R)-ethyl 2-[2’-(2’’-iodoethyl)phenoxy]propanoate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以27%的产率得到rac-ethyl 2-methylchroman-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
• 作为产物：
  描述：

  ethyl (R)-2-(2-(2-methoxyvinyl)phenoxy)propanoate 在 咪唑 、 sodium tetrahydroborate 、 水 、 碘 、 三苯基膦 、 copper dichloride 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 生成 (2R)-ethyl 2-[2’-(2’’-iodoethyl)phenoxy]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