<3(2S),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-<3-(trifluoromethyl)phenoxy>propanoyl>-4-benzyloxazolidin-2-one | 236110-96-6

• 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: <3(2S),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-<3-(trifluoromethyl)phenoxy>propanoyl>-4-benzyloxazolidin-2-one
• 英文别名: <3(2S),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-(3-trifluoromethyl)phenoxypropanoyl>-4-benzyloxazolidin-2-one；(4S)-3-[(2S)-3-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-[3-(trifluoromethyl)phenoxy]propanoyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS: 236110-96-6
• 化学式: C₃₆H₃₂F₃N₃O₆
• 分子量: 659.662
• InChiKey: BCNPTXQHPCIWIX-UCGGBYDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  <3(2S),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-<3-(trifluoromethyl)phenoxy>propanoyl>-4-benzyloxazolidin-2-one 在 盐酸 、 sodium methylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.33h， 生成 (S)-(-)-3-<4-<2-ethoxy>phenyl>-2-<3-(trifluoromethyl)phenoxy>propanoic 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,3RS),4S>-3-<3-<4-<2-ethoxy>phenyl>-3-hydroxy-2-(3-trifluoromethyl)phenoxypropanoyl>-4-benzyloxazolidin-2-one 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 60.0h， 以64%的产率得到<3(2S),4S>-3-<3-<4-<2-ethoxy>phenyl>-2-<3-(trifluoromethyl)phenoxy>propanoyl>-4-benzyloxazolidin-2-one
  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

文献信息

• Non-thiazolidinedione antihyperglycaemic agents. Part 5: Asymmetric aldol synthesis of (S)-(−)-2-oxy-3-arylpropanoic acids
  作者：David Haigh、Helen C Birrell、Barrie C.C Cantello、Drake S Eggleston、R.Curtis Haltiwanger、Richard M Hindley、Anantha Ramaswamy、Nicola C Stevens

  DOI：10.1016/s0957-4166(99)00112-3

  日期：1999.4

  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.
• Non-thiazolidinedione antihyperglycaemic agents. Part 4: Synthesis of (±)-, (R)-(+)- and (S)-(−)-enantiomers of 2-oxy-3-arylpropanoic acids
  作者：David Haigh、Helen C Birrell、Barrie C.C Cantello、Richard M Hindley、Anantha Ramaswamy、Harshad K Rami、Nicola C Stevens

  DOI：10.1016/s0957-4166(99)00104-4

  日期：1999.4

  The synthesis of a new series of potent 2-oxy-3-arylpropanoic acid antihyperglycaemic agents in both racemic and non-racemic form is described. Resolution of racemic acids 1 is accomplished via amide formation with either (S)-2-phenylglycinol or (S)-4-benzyloxazolidin-2-one as complementary resolving agents. (C) 1999 Elsevier Science Ltd. All rights reserved.