(SR,1S,2R)-1-(tert-butylsulfinyl)2-(hydroxymethyl)ferrocene | 189164-87-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: (SR,1S,2R)-1-(tert-butylsulfinyl)2-(hydroxymethyl)ferrocene
• 英文别名: (SR,1S,2R)-2-(tert-butylsulfinyl)ferrocenylmethanol；[5-[(S)-tert-butylsulfinyl]cyclopenta-1,3-dien-1-yl]methanol;cyclopenta-1,3-diene;iron(2+)
• CAS: 189164-87-2；180293-09-8；180293-10-1
• 化学式: C₁₅H₂₀FeO₂S
• 分子量: 320.236
• InChiKey: RJUSLVKKYQTXPW-GXKRWWSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (R)-S-tert-butylferrocenesulfoxide 、 水 在 2,4,6-triisopropylphenyl lithium 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(SR,1S,2R)-1-(tert-butylsulfinyl)2-(hydroxymethyl)ferrocene
  参考文献：
  名称：

  (SR,1R,2S)-1-(tert-Butylsulfinyl)2-(hydroxymethyl)ferrocene

  摘要：

  From the reaction of (SR)-(-)-tert-butylsulfinylferrocene with (2,4,6-triisopropylphenyl)lithium followed by paraformaldehyde, the title compound, [Fe(C5H5)(C10H15O2S)], was obtained as an unexpected by-product along with the major product, (SR,1S,2R)-2-(tert-butylsulfinyl)ferrocenylmethanol. The absolute structure of this byproduct could not be ascertained via NMR, but it was characterized by X-ray diffraction as (SR,1R,2S)-2-(tert-butylsulfinyl )ferrocenylmethanol, a diastereoisomer of the major product. The two cyclopentadienyl rings are rotated away from one another by 25.5(5)degrees (from an eclipsed form towards a gauche form), in contrast to the mutually eclipsed rings generally found in monosubstituted ferrocenes. Hydrogen bonding between sulfoxide O atoms and hydroxyl H atoms produces infinite one-dimensional chains.

  DOI：

  10.1107/s0108270196014916