syn-2-Fluoro-3-methyl-4-pentenoic acid | 98064-45-0

• 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: syn-2-Fluoro-3-methyl-4-pentenoic acid
• 英文别名: (2S,3R)-2-fluoro-3-methylpent-4-enoic acid
• CAS: 98064-45-0
• 化学式: C₆H₉FO₂
• 分子量: 132.135
• InChiKey: DBOXMANNAFULMX-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-2-Fluoro-3-methyl-4-pentenoic acid 在 碘 、 silver(I) acetate 作用下， 反应 16.0h， 以78%的产率得到4,5-dihydro-3-fluoro-5-(iodomethyl)-4-methyl-2(3H)-furanone
  参考文献：
  名称：

  The synthesis of 2,3-dideoxy-2-fluoro-3-C-methylpentose-containing nucleosides via [3,3]-sigmatropic rearrangements

  摘要：

  [3,3]-Sigmatropic rearrangement of in situ-formed [0,0]-silyl ketene acetals of butenyl fluoroacetates was used as the key step in the synthesis of racemic 2,3-dideoxy-2-fluoro-3-C-methylpentofuranoses. The product pentofuranoses were transformed further into pyrimidine and purine nucleosides. The conformations of the synthetic carbohydrates were confirmed by single-crystal X-ray diffraction studies and indicated that previous structural assignments made by NMR were in error.

  DOI：

  10.1016/0008-6215(93)84067-g
• 作为产物：
  描述：

  (Z)-2-buten-1-yl fluoroacetate 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 syn-2-Fluoro-3-methyl-4-pentenoic acid
  参考文献：
  名称：

  Peptide modification by incorporation of α-trifluoromethyl substituted α-amino acids

  摘要：

  DOI：

  10.1016/s0022-1139(00)83708-2

文献信息

• Claisen rearrangement of allylfluorovinyl ethers
  作者：Frédérique Tellier、Max Audouin、Monique Baudry、Raymond Sauvêtre

  DOI：10.1016/s0022-1139(98)00313-3

  日期：1999.2

  Synthesis of α-fluoro β-substituted γ-unsaturated acid derivatives via a diastereoselective Claisen rearrangement of allyldifluorovinyl ethers is described.

  描述了通过烯丙基二氟乙烯基醚的非对映选择性克莱森重排合成α-氟β-取代的γ-不饱和酸衍生物。
• An improved procedure for the ireland-claisen rearrangement of allyl fluoroacetates
  作者：Koichi Araki、John T. Welch

  DOI：10.1016/s0040-4039(00)77586-1

  日期：1993.4

  The Ireland-Claisen rearrangement of allyl flouroacetates was effected by treatment of the starting esters with trialkylsilyltriflates in the presence of tertiary amines. The stereoselective formation of the products was rationalized as resulting from equilibration of the stereochemistry of the silyl ester products under the reaction conditions.

  氟乙酸烯丙酯的爱尔兰-克莱森重排是通过在叔胺存在下用三烷基甲硅烷基三氟甲磺酸酯处理起始酯来实现的。产物的立体选择性形成是合理的，这是由于在反应条件下甲硅烷基酯产物的立体化学平衡所致。
• Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates
  作者：John T. Welch、Janet S. Plummer、Tso Sheng Chou

  DOI：10.1021/jo00001a065

  日期：1991.1

  The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.
• The synthesis of 2,3-dideoxy-2-fluoro-3-C-methylpentose-containing nucleosides via [3,3]-sigmatropic rearrangements
  作者：Koichi Araki、Wei Oin Yun、John O'Toole、Paul J. Toscano、John T. Welch

  DOI：10.1016/0008-6215(93)84067-g

  日期：1993.10

  [3,3]-Sigmatropic rearrangement of in situ-formed [0,0]-silyl ketene acetals of butenyl fluoroacetates was used as the key step in the synthesis of racemic 2,3-dideoxy-2-fluoro-3-C-methylpentofuranoses. The product pentofuranoses were transformed further into pyrimidine and purine nucleosides. The conformations of the synthetic carbohydrates were confirmed by single-crystal X-ray diffraction studies and indicated that previous structural assignments made by NMR were in error.
• Peptide modification by incorporation of α-trifluoromethyl substituted α-amino acids
  作者：Klaus Burger、Norbert Sewald、Christian Schierlinger、Kerstin Mütze、Liza C. Seymour

  DOI：10.1016/s0022-1139(00)83708-2

  日期：1991.9