(S)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)hex-4-ynamide | 1237025-20-5

• 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: (S)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)hex-4-ynamide
• 英文别名: (3S)-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methyl-3-[4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]hex-4-ynamide
• CAS: 1237025-20-5
• 化学式: C₃₆H₃₄F₃NO₃
• 分子量: 585.666
• InChiKey: HYBDYAJGVFZASU-NKOFKNPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)hex-4-ynamide 、 碳酸二甲酯 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester
  参考文献：
  名称：

  Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

  摘要：

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.019
• 作为产物：
  描述：

  (S)-3-(4-(3-bromobenzyloxy)phenyl)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methylhex-4-ynamide 、 4-三氟甲基苯硼酸 在 potassium phosphate monohydrate 、 palladium diacetate 、 三环己基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以0.69 g的产率得到(S)-N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)hex-4-ynamide
  参考文献：
  名称：

  Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

  摘要：

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.019

文献信息

• Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation
  作者：Jacqueline C.S. Woo、Sheng Cui、Shawn D. Walker、Margaret M. Faul

  DOI：10.1016/j.tet.2010.04.019

  日期：2010.6

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.