(S)-2,2-dimethyl-5-(1-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)but-2-ynyl)-1,3-dioxane-4,6-dione | 1237025-63-6

• 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: (S)-2,2-dimethyl-5-(1-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)but-2-ynyl)-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-[(1S)-1-[4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]but-2-ynyl]-1,3-dioxane-4,6-dione
• CAS: 1237025-63-6
• 化学式: C₃₀H₂₅F₃O₅
• 分子量: 522.521
• InChiKey: GQORRGNTKOYNPC-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2,2-dimethyl-5-(1-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)but-2-ynyl)-1,3-dioxane-4,6-dione 在 水 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 水 、 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到sodium (S)-3-(4-{[4'-(trifluoromethyl)biphenyl-3-yl]methoxy}phenyl)hex-4-ynoate
  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：

  5-[(1S)-1-[4-[(3-bromophenyl)methoxy]phenyl]but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione 、 4-三氟甲基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate monohydrate 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 以17%的产率得到(S)-2,2-dimethyl-5-(1-(4-((4'-(trifluoromethyl)biphenyl-3-yl)methoxy)phenyl)but-2-ynyl)-1,3-dioxane-4,6-dione
  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.