4,5-dihydro-3-fluoro-5-(iodomethyl)-4-methyl-2(3H)-furanone | 98064-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4,5-dihydro-3-fluoro-5-(iodomethyl)-4-methyl-2(3H)-furanone
• 英文别名: (3R,4S,5R)-3-Fluoro-5-iodomethyl-4-methyl-dihydro-furan-2-one；(3R,4S,5R)-3-fluoro-5-(iodomethyl)-4-methyloxolan-2-one
• CAS: 98064-47-2
• 化学式: C₆H₈FIO₂
• 分子量: 258.031
• InChiKey: RLHIQTNUVONBRY-VAYJURFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-3-fluoro-5-(iodomethyl)-4-methyl-2(3H)-furanone 生成 2-fluoro-5-iodo-3-C-methyl-2,3,5-trideoxypentofuranose
  参考文献：
  名称：

  WELCH, J. T.;SAMARTINO, J. S., J. ORG. CHEM., 1985, 50, N 19, 3663-3665

  摘要：

  DOI：
• 作为产物：
  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

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。
• 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.
• WELCH, JOHN T.;PLUMMER, JANET S.;CHOU, TSO-SHENG, J. ORG. CHEM., 56,(1991) N, C. 353-359
  作者：WELCH, JOHN T.、PLUMMER, JANET S.、CHOU, TSO-SHENG

  DOI：——

  日期：——