2-[pentafluorophenyl(pyrrolidin-1-yl)methyl]phenol

• 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: 2-[pentafluorophenyl(pyrrolidin-1-yl)methyl]phenol
• 英文别名: 2-[(2,3,4,5,6-Pentafluorophenyl)-pyrrolidin-1-ylmethyl]phenol
• 化学式: C₁₇H₁₄F₅NO
• 分子量: 343.296
• InChiKey: CXHLAXSXXGLHLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯三(2,3,4,5,6-五氟苯基)硅烷 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 16.08h， 生成 2-[pentafluorophenyl(pyrrolidin-1-yl)methyl]phenol
  参考文献：
  名称：

  Synthesis of Pentafluorophenylmethylamines via Silicon Mannich Reaction

  摘要：

  The three-component coupling of aldehydes, secondary amines, and methoxytris(pentafluorophenyl)silane, MeOSi(C6F5)(3), affording pentafluorophenylmethylamines has been described. The generation of the five-coordinate silicate intermediate is believed to be the key feature responsible for the efficiency of the reaction.

  DOI：

  10.1021/ol050845l

文献信息

• Reactions of salicylaldehyde with tris(pentaf luorophenyl)silanes and secondary amines
  作者：A. D. Dilman、D. E. Arkhipov、P. A. Belyakov、M. I. Struchkova、V. A. Tartakovsky

  DOI：10.1007/s11172-006-0285-0

  日期：2006.3

  Reactions of tris(pentafluorophenyl)silanes RSi(C6F5)3 with salicylaldehyde and secondary amines were studied. The reactions afforded α-pentafluorophenyl-substituted amines. Silanes RSi(C6F5)3 (R = Me, Ph, C6F5, CH2CH=CH2, and CH=CH2) were found to be efficient reagents for transfer of the C6F5 group to the iminium cation generated from salicylaldehyde and amine. However, tris(pentafluorophenyl)phenylethynyl-and tris(pentafluorophenyl)silanes were not able to serve as a source of a fluorinated substituent because of competitive transfer of acetylenide fragment or hydride.

  研究了三(五氟苯基)硅烷 RSi(C6F5)3 与水杨醛和仲胺的反应。反应生成了 α-五氟苯基取代胺。研究发现硅烷 RSi( )3（R = Me、Ph、 、 CH=CH2 和 CH= ）是将 基团转移到由水杨醛和胺生成的亚胺阳离子上的有效试剂。然而，三（五氟苯基）苯乙炔和三（五氟苯基）硅烷由于乙炔片段或氢化物的竞争性转移而不能作为氟化取代基的来源。