4-octanone-3,3,5,5-d4 | 10258-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-octanone-3,3,5,5-d4
• 英文别名: <3,3-2H2-5,5-2H2>-Oktan-4-on；4-Octanon-3,3,5,5-d(4)；3,3,5,5-tetradeuterio-octan-4-one
• CAS: 10258-85-2
• 化学式: C₈H₁₆O
• 分子量: 132.183
• InChiKey: YWXLSHOWXZUMSR-KXGHAPEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  9.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-辛酮 在 重水 作用下， 生成 4-octanone-3,3,5,5-d4
  参考文献：
  名称：

  Stereochemical Analysis of Deuterated Alkyl Chains by MS/MS

  摘要：

  Vicinally deuterated sec-alkyl phenyl ethers, CH3(CH2)(m)CH(OPh)CHD(CH2)nCH(3), display significant differences in mass spectra between three and erythro stereoisomers. MS/MS experiments, in which parent ions of a single mass are selected and their fragmentation patterns subsequently measured, show that alkene expulsion represents virtually the only decomposition pathway. Two types of MS/MS experiment are reported: mass-analyzed ion kinetic energy (MIKE) spectroscopy of metastable ions and collisionally activated decomposition (CAD) of stable ions. The expulsion of a deuterated alkene from a monodeuterated precursor yields ionized phenol, PhOH.+ (m/z 94). The expulsion of an undeuterated alkene yields PhOD.+ (m/z 95). Without exception, the ratios (PhOD.+/ PhOH.+) from precursors in the three series have values greater than their diastereomers in the erythro series. The ratio of ratios, r = PhOD.+/PhOH.+ for the three divided by PhOD.+/PhOH.+ for the erythro, has a value of 1.2 for the 2-phenoxy-3-deuteriobutanes and larger values for all of the higher homologues up through the monodeuterated phenoxyoctanes (m + n = 4). The highest degree of stereoselectivity, r = 5.8, is measured for 3-phenoxy-4-deuteriohexane. Experiments with multiply deuterated analogues show that alkene elimination is highly regioselective, unlike the corresponding decompositions of ionized sec-alcohols or their acetates. The fact that a large fraction of ionized sec-alkyl phenyl ethers undergo stereospecific syn-elimination means that mass spectrometry has a useful capacity to distinguish one isotopically labeled diastereomer from another.

  DOI：

  10.1021/jo9912247

文献信息

• Stereochemical Analysis of Deuterated Alkyl Chains by MS/MS
  作者：J. P. Morizur、M. H. Taphanel、Philip S. Mayer、Thomas Hellman Morton

  DOI：10.1021/jo9912247

  日期：2000.1.1

  Vicinally deuterated sec-alkyl phenyl ethers, CH3(CH2)(m)CH(OPh)CHD(CH2)nCH(3), display significant differences in mass spectra between three and erythro stereoisomers. MS/MS experiments, in which parent ions of a single mass are selected and their fragmentation patterns subsequently measured, show that alkene expulsion represents virtually the only decomposition pathway. Two types of MS/MS experiment are reported: mass-analyzed ion kinetic energy (MIKE) spectroscopy of metastable ions and collisionally activated decomposition (CAD) of stable ions. The expulsion of a deuterated alkene from a monodeuterated precursor yields ionized phenol, PhOH.+ (m/z 94). The expulsion of an undeuterated alkene yields PhOD.+ (m/z 95). Without exception, the ratios (PhOD.+/ PhOH.+) from precursors in the three series have values greater than their diastereomers in the erythro series. The ratio of ratios, r = PhOD.+/PhOH.+ for the three divided by PhOD.+/PhOH.+ for the erythro, has a value of 1.2 for the 2-phenoxy-3-deuteriobutanes and larger values for all of the higher homologues up through the monodeuterated phenoxyoctanes (m + n = 4). The highest degree of stereoselectivity, r = 5.8, is measured for 3-phenoxy-4-deuteriohexane. Experiments with multiply deuterated analogues show that alkene elimination is highly regioselective, unlike the corresponding decompositions of ionized sec-alcohols or their acetates. The fact that a large fraction of ionized sec-alkyl phenyl ethers undergo stereospecific syn-elimination means that mass spectrometry has a useful capacity to distinguish one isotopically labeled diastereomer from another.