(S)-6-(4-bromophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one | 1258203-98-3

• 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)-6-(4-bromophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one
• 英文别名: (S)-6-(iodomethyl)-6-(p-bromophenyl)tetrahydro-2H-pyran-2-one；6-(4-bromophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one；(6S)-6-(4-bromophenyl)-6-(iodomethyl)oxan-2-one
• CAS: 1258203-98-3
• 化学式: C₁₂H₁₂BrIO₂
• 分子量: 395.035
• InChiKey: KGZNRKRNPYFTPF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(4-bromophenyl)hex-5-enoic acid 在 4-fluoro-N-iodophthalimide 、 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(dipentylamino)cyclohexyl)urea 、 碘 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以71%的产率得到(S)-6-(4-bromophenyl)-6-(iodomethyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  叔氨基脲催化的对映选择性碘内酯化

  摘要：

  结合阴离子：使用叔氨基脲催化剂实现了 5-己烯酸的高度对映选择性碘内酯化（参见方案）。在该过程中使用催化碘对于提高化学计量 I +源的反应性和对映选择性至关重要。该机制被认为涉及通过氢键供体催化剂结合亚胺酸碘鎓中间体。

  DOI：

  10.1002/anie.201003681

文献信息

• Asymmetric Iodolactonization Utilizing Chiral Squaramides
  作者：Jørn E. Tungen、Jens M. J. Nolsøe、Trond V. Hansen

  DOI：10.1021/ol302798g

  日期：2012.12.7

  Asymmetric iodolactonization of gamma- and delta-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding iodolactones 2 with up to 96% ee. By this protocol, unsaturated carboxylic acids are converted enantioselectively to synthetically useful delta-lactones in high yields using commercially available NIS. Apparently, both hydrogen bonding and aryl/aryl interactions are important for efficient stereodifferentiation.
• An asymmetric iodolactonization reaction catalyzed by a zinc bis-proline–phenol complex
  作者：Liudmila Filippova、Yngve Stenstrøm、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2013.11.028

  日期：2014.1

  The intramolecular zinc bis-proline-phenol complex 2a was found to promote enantioselective iodolactonization reactions of both electron-rich and electron-poor 5-aryl-5-hexenoic acids affording delta-iodolactones in good chemical yields with up to 82% enantiomeric excess. The reactions were found to be insensitive to air and moisture, providing an experimentally simple protocol for synthetically useful compounds. (C) 2013 Elsevier Ltd. All rights reserved.