3-pentanol-2,2,4,4-d4 | 65130-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-pentanol-2,2,4,4-d4
• 英文别名: Pentan-2,2,4,4-D4-3-OL；2,2,4,4-tetradeuteriopentan-3-ol
• CAS: 65130-53-2
• 化学式: C₅H₁₂O
• 分子量: 92.1179
• InChiKey: AQIXEPGDORPWBJ-KHORGVISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  6.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-pentanol-2,2,4,4-d4 在 溴 、 三苯基膦 作用下， 生成 2,2,4,4-Tetradeuterio-3-pentylbromid
  参考文献：
  名称：

  Unimolecular reactions of ionized alkanes

  摘要：

  DOI：

  10.1021/ja00399a033
• 作为产物：
  描述：

  3-戊酮-D4 在 lithium aluminium tetrahydride 作用下， 生成 3-pentanol-2,2,4,4-d4
  参考文献：
  名称：

  Unimolecular reactions of ionized alkanes

  摘要：

  DOI：

  10.1021/ja00399a033

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.
• Alkane elimination from ionized alkanols
  作者：John L. Holmes、Peter C. Burgers、Yousuf A. Mollah

  DOI：10.1002/oms.1210170305

  日期：1982.3

  AbstractThe energetics, metastable characteristics and daughter ion structures for the loss of small alkane molecules from ionized 2‐propanol, 2‐butanol and 3‐pentanol have been examined in detail. [2‐Propanol]+˙ ions lose CH4 to generate the keto and enol forms of [C2H4O]+˙ and the same daughter ions are produced by loss of C2H6 from [2‐butanol]+˙. Ionized 3‐pentanol does not lose CH4 but readily eliminates C2H6 to produce the enol ion [CH3CHCHOH]+˙. The last reaction was shown to proceed by a simple 1,2 elimination mechanism in the μs time‐frame; isotope effects are also discussed.
• OHTA, NOBUAKI;YANO, AKIHIKO;OKAMOTO, HIDESHI;ICHIKAWA, TAKAHISA, BULL. FAC. ENG. HIROSHIMA UNIV., 1986, 34, N 2, 155-158
  作者：OHTA, NOBUAKI、YANO, AKIHIKO、OKAMOTO, HIDESHI、ICHIKAWA, TAKAHISA

  DOI：——

  日期：——