(R)-1-cyano-1-<3-4(fluorophenoxy)phenyl>methyl acetate | 143621-74-3

• 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: (R)-1-cyano-1-<3-4(fluorophenoxy)phenyl>methyl acetate
• CAS: 143621-74-3
• 化学式: C₁₆H₁₂FNO₃
• 分子量: 285.275
• InChiKey: VRYHAHKCJXKUEG-INIZCTEOSA-N

物化性质

• 沸点：
  392.7±42.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酸异丙烯酯 、 3-(4-氟苯氧基)苯甲醛 、 丙酮氰醇 在 3 A molecular sieve 、 anion-exchange resin IRA-904 (OH-) 作用下， 以 异丙醚 为溶剂， 反应 72.0h， 生成 (R)-1-cyano-1-<3-4(fluorophenoxy)phenyl>methyl acetate 、 (S)-(+)-1-cyano-1-<3-(4-fluorophenoxy)phenyl>methyl acetate
  参考文献：
  名称：

  One-pot synthesis of optically active cyanohydrin acetates from aldehydes via lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins

  摘要：

  A novel one-pot synthesis of optically active cyanohydrin acetates from aldehydes has been accomplished by lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins in an organic solvent. Racemic cyanohydrins 2, generated from aldehydes 1 and acetone cyanohydrin in diisopropyl ether under the catalysis of basic anion-exchange resin (OH- form), were acetylated stereoselectively by a lipase from Pseudomonas cepacia (Amano) with isopropenyl acetate as an acylating reagent. The (S)-isomer of 2 was preferentially acetylated by the lipase, while the unreacted (R)-isomer was continuously racemized through reversible transhydrocyanation catalyzed by the resin. These processes thus enabled one-stage conversion of various aldehydes 1a-n into the corresponding (S)-cyanohydrin acetates 3a-n with up to 94% ee in 63-100% conversion yields. The racemization of the optically active cyanohydrin 2e by Amberlite IRA-904 (OH- form) was found to be much faster than the enzymatic acetylation, confirming the effective second-order asymmetric transformation. Enzymatic deacetylation of (S)-cyanohydrin acetates in an organic solvent and the synthesis of optically active pyrethroids are also described.

  DOI：

  10.1021/jo00047a016