<2-d1>-2-fluoro-<1-13C>-1-phenoxypropane | 134757-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: <2-d1>-2-fluoro-<1-13C>-1-phenoxypropane
• 英文别名: [2-d1]-2-fluoro-[1-13C]-1-phenoxypropane
• CAS: 134757-58-7
• 化学式: C₉H₁₁FO
• 分子量: 156.165
• InChiKey: YXSPLDZGKWOKEG-JOFCMPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  sodium phenoxide 在 lithium aluminium deuteride 、 二乙胺基三氟化硫 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 <2-d1>-2-fluoro-<1-13C>-1-phenoxypropane
  参考文献：
  名称：

  Isotopomer distributions of neutral products from a doubly labeled cation in the gas phase. Interconversion of 1-fluoro-1-propyl cation and 1-fluoroisopropyl cation on the C3H6F+ potential energy surface

  摘要：

  The title cations CH3CH2CHF+ (3) and CH3CHCH2F+ (4) are formed as transient intermediates in the gas phase. These are labile on the millisecond timescale as free ions but can be intercepted in ion-neutral complexes. When 3 is generated as a free cation by reaction of CF3+ with propionaldehyde, it rearranges to (CH3)2CF+ (1), as shown by recovery of 2-fluoropropene as a neutral product from its deprotonation in an EBFlow experiment. The same neutral product is recovered when 1 is produced directly by reaction of acetone with CF3+ in the EBFlow. Neutral products indicative of 3 and 4 (allyl fluoride and 1-fluoropropene) are recovered when these cations are formed in [R+ PhO.] ion-neutral complexes by electron bombardment of CH3CDFCH2OPh (6). Analysis of the isotopic distribution in the recovered neutrals from EBFlow radiolysis of CH3CDF*CH2OPh (where the asterisked carbon is C-13-labeled) allows an assessment of the primary rearrangement pathways. The distribution of label is assayed by using F-19 NMR. Rearrangement of the R+ moiety to form deuterated 1 occurs in about half of the complexes formed. In the remainder, methyl transfer (to form deuterated 3) is 2-3 times faster than fluoride transfer (to form deuterated 4). Scrambling of deuterium in the neutral products provides evidence that 3 and 4 interconvert within the ion-neutral complexes.

  DOI：

  10.1021/ja00018a009

文献信息

• Isotopomer distributions of neutral products from a doubly labeled cation in the gas phase. Interconversion of 1-fluoro-1-propyl cation and 1-fluoroisopropyl cation on the C3H6F+ potential energy surface
  作者：Thomas A. Shaler、Thomas Hellman Morton

  DOI：10.1021/ja00018a009

  日期：1991.8

  The title cations CH3CH2CHF+ (3) and CH3CHCH2F+ (4) are formed as transient intermediates in the gas phase. These are labile on the millisecond timescale as free ions but can be intercepted in ion-neutral complexes. When 3 is generated as a free cation by reaction of CF3+ with propionaldehyde, it rearranges to (CH3)2CF+ (1), as shown by recovery of 2-fluoropropene as a neutral product from its deprotonation in an EBFlow experiment. The same neutral product is recovered when 1 is produced directly by reaction of acetone with CF3+ in the EBFlow. Neutral products indicative of 3 and 4 (allyl fluoride and 1-fluoropropene) are recovered when these cations are formed in [R+ PhO.] ion-neutral complexes by electron bombardment of CH3CDFCH2OPh (6). Analysis of the isotopic distribution in the recovered neutrals from EBFlow radiolysis of CH3CDF*CH2OPh (where the asterisked carbon is C-13-labeled) allows an assessment of the primary rearrangement pathways. The distribution of label is assayed by using F-19 NMR. Rearrangement of the R+ moiety to form deuterated 1 occurs in about half of the complexes formed. In the remainder, methyl transfer (to form deuterated 3) is 2-3 times faster than fluoride transfer (to form deuterated 4). Scrambling of deuterium in the neutral products provides evidence that 3 and 4 interconvert within the ion-neutral complexes.