(S)-6-(iodomethyl)-6-(naphthalen-2-yl)tetrahydro-2H-pyran-2-one | 1258203-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-6-(iodomethyl)-6-(naphthalen-2-yl)tetrahydro-2H-pyran-2-one
• 英文别名: (6S)-6-(iodomethyl)-6-naphthalen-2-yloxan-2-one
• CAS: 1258203-94-9
• 化学式: C₁₆H₁₅IO₂
• 分子量: 366.198
• InChiKey: YHVGKTLJIDYBHC-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-(naphthalen-2-yl)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92%的产率得到(S)-6-(iodomethyl)-6-(naphthalen-2-yl)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.
• The Role of Ni-Carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2
  作者：Takayoshi Arai、Satoshi Kajikawa、Eri Matsumura

  DOI：10.1055/s-0033-1339676

  日期：——

  The combination of a PyBidine-Ni(OAc)(2) complex with a catalytic amount of iodine efficiently catalyzed asymmetric iodolactonization to generate chiral iodolactones with up to 89% enantiomeric excess. The formation of an intermediate Ni-carboxylate species from the alkenyl carboxylic acid is a key role in promoting the iodolactonization.