2,2,4,4-tetradeuterio-hexan-3-one | 24588-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,4,4-tetradeuterio-hexan-3-one
• 英文别名: (2.2.4.4-D4)Hexanon-(3)；3-Hexanone-2,2,4,4-d4；2,2,4,4-tetradeuteriohexan-3-one
• CAS: 24588-54-3
• 化学式: C₆H₁₂O
• 分子量: 104.129
• InChiKey: PFCHFHIRKBAQGU-CQOLUAMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  7.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,2,4,4-tetradeuterio-hexan-3-one 、 二碘甲烷 生成 2,2,4,4-tetradeuterio-3-methylidenehexane
  参考文献：
  名称：

  OHTA, NOBUAKI;ENDO, MASATO;ICHIKAWA, TAKAHISA, BULL. FAC. ENG. HIROSHIMA UNIV., 1985, 33, N 2, 143-148

  摘要：

  DOI：
• 作为产物：
  描述：

  3-己酮 在 重水 作用下， 生成 2,2,4,4-tetradeuterio-hexan-3-one
  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