ethyl (2Z)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropent-2-enoate | 812675-89-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2Z)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropent-2-enoate
• 英文别名: (2Z)-5-[[(1,1-dimethylethyl)di-methylsilyl]oxy]-2-fluoro-2-pentenoic acid ethyl ester；ethyl (Z)-5-[tert-butyl(dimethyl)silyl]oxy-2-fluoropent-2-enoate
• CAS: 812675-89-1
• 化学式: C₁₃H₂₅FO₃Si
• 分子量: 276.424
• InChiKey: JINVTOCRUUCTMW-LUAWRHEFSA-N

物化性质

• 沸点：
  293.4±40.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropent-2-enoate 、 (2E)-5-[[(1,1-dimethylethyl)di-methylsilyl]oxy]-2-fluoro-2-pentenoic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.5h， 生成 (2E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropent-2-en-1-ol 、 (2Z)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-fluoro-2-penten-1-ol
  参考文献：
  名称：

  [EN] METHODS FOR TREATMENT AND PREVENTION OF GASTROINTESTINAL CONDITIONS
  [FR] PROCEDES DESTINES AU TRAITEMENT ET A LA PREVENTION DE TROUBLES GASTRO-INTESTINAUX

  摘要：

  公开号：

  WO2004012726A3
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 3-(叔丁基-二甲基-硅烷基OXY)-丙醛 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以30.5%的产率得到(2E)-5-[[(1,1-dimethylethyl)di-methylsilyl]oxy]-2-fluoro-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines

  摘要：

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.030

文献信息

• [EN] METHODS FOR TREATMENT AND PREVENTION OF GASTROINTESTINAL CONDITIONS<br/>[FR] PROCEDES DESTINES AU TRAITEMENT ET A LA PREVENTION DE TROUBLES GASTRO-INTESTINAUX
  申请人：PHARMACIA CORP

  公开号：WO2004012726A3

  公开（公告）日：2004-06-03
• 3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines
  作者：Alan E. Moormann、Jane L. Wang、Katherine E. Palmquist、Michele A. Promo、Jeffery S. Snyder、Jeffrey A. Scholten、Mark A. Massa、James A. Sikorski、R. Keith Webber

  DOI：10.1016/j.tet.2004.09.030

  日期：2004.11

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.