(S)-(-)-3-<4-<2-ethoxy>phenyl>-2-ethoxypropanoic acid methyl ester | 236110-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (S)-(-)-3-<4-<2-ethoxy>phenyl>-2-ethoxypropanoic acid methyl ester
• CAS: 236110-97-7
• 化学式: C₂₂H₂₆N₂O₅
• 分子量: 398.459
• InChiKey: WTAWDUZOFWROBE-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.03
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-3-<4-<2-ethoxy>phenyl>-2-ethoxypropanoic acid methyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以86%的产率得到(S)-(-)-3-<4-<2-ethoxy>phenyl>-2-ethoxypropanoic acid
  参考文献：
  名称：

  Non-thiazolidinedione antihyperglycaemic agents. Part 5: Asymmetric aldol synthesis of (S)-(−)-2-oxy-3-arylpropanoic acids

  摘要：

  Boron-mediated asymmetric aldol reactions of substituted benzaldehyde 5 with 2-oxyethanoyloxazolidinones 4a-e, containing electron withdrawing, chelating, and bulky alkoxy and aryloxy groups, gave variable yields of synaldol adducts 6a-e in high diastereoisomeric excess. Dehydroxylation of these adducts afforded 7a-e in a sequence which complements the traditional Evans asymmetric alkylation strategy. Cleavage of the auxiliary from 7a-e afforded antihyperglycaemic (S)-(-)-2-oxy-3-arylpropanoic acids 3a-e in excellent enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00112-3
• 作为产物：
  描述：

  <3(2S,3R),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-ethoxy-3-hydroxypropanoyl>-4-benzyloxazolidin-2-one 在 三乙基硅烷 、 sodium methylate 、 三氟乙酸 作用下， 反应 62.33h， 生成 (S)-(-)-3-<4-<2-ethoxy>phenyl>-2-ethoxypropanoic acid methyl ester
  参考文献：
  名称：

  Non-thiazolidinedione antihyperglycaemic agents. Part 5: Asymmetric aldol synthesis of (S)-(−)-2-oxy-3-arylpropanoic acids

  摘要：

  Boron-mediated asymmetric aldol reactions of substituted benzaldehyde 5 with 2-oxyethanoyloxazolidinones 4a-e, containing electron withdrawing, chelating, and bulky alkoxy and aryloxy groups, gave variable yields of synaldol adducts 6a-e in high diastereoisomeric excess. Dehydroxylation of these adducts afforded 7a-e in a sequence which complements the traditional Evans asymmetric alkylation strategy. Cleavage of the auxiliary from 7a-e afforded antihyperglycaemic (S)-(-)-2-oxy-3-arylpropanoic acids 3a-e in excellent enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00112-3