3-(Ethyl)<4-13C₁-4,4,5,5,5-D5>pentan-2-one | 141305-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(Ethyl)<4-13C₁-4,4,5,5,5-D5>pentan-2-one
• CAS: 141305-27-3
• 化学式: C₇H₁₄O
• 分子量: 125.097
• InChiKey: GSNKRSKIWFBWEG-QOMIIBKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  8.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  3-(Ethyl)<4-13C₁-4,4,5,5,5-D5>pentan-2-one 在 氘氧化钠 、 重水 作用下， 反应 26.0h， 以22 mg的产率得到3-(Ethyl)<4-13C₁-D9>pentan-2-one
  参考文献：
  名称：

  Is the McLafferty rearrangement of ketones concerted or stepwise? The application of kinetic isotope effects

  摘要：

  AbstractIntramolecular 13C and 2H isotope effects have been measured for unimolecular losses of ethene (the McLafferty rearrangement) from metastable molecular ions of 2‐ethyl‐1‐phenylbutanl‐1‐one, 3‐ethylpentan‐2‐one and heptan‐4‐one. Primary and secondary deuterium isotope effects are observed at the γ‐(terminal) and β‐positions, respectively. Large primary 13C isotope effects occur at β‐positions and for the y positions of γ‐ethylpentan‐2‐one and heptan‐4‐one. The carbon isotope effects in the cases of the doubly isotopically labelled CH3COCH(C2H5)(13CH2CH3) and CD3COCD(C2D5)(13CD2CD3) are 1.17 (±0.01) and 1.04 (±0.01), respectively. All of these isotope effects are consistent with a stepwise mechanism in which more than one step is rate determining.

  DOI：

  10.1002/oms.1210270319
• 作为产物：
  描述：

  Ethyl α-(ethyl)-α-(<1-13C₁-D5>ethyl)acetoacetate 在 氢氧化钾 作用下， 以31%的产率得到3-(Ethyl)<4-13C₁-4,4,5,5,5-D5>pentan-2-one
  参考文献：
  名称：

  Is the McLafferty rearrangement of ketones concerted or stepwise? The application of kinetic isotope effects

  摘要：

  AbstractIntramolecular 13C and 2H isotope effects have been measured for unimolecular losses of ethene (the McLafferty rearrangement) from metastable molecular ions of 2‐ethyl‐1‐phenylbutanl‐1‐one, 3‐ethylpentan‐2‐one and heptan‐4‐one. Primary and secondary deuterium isotope effects are observed at the γ‐(terminal) and β‐positions, respectively. Large primary 13C isotope effects occur at β‐positions and for the y positions of γ‐ethylpentan‐2‐one and heptan‐4‐one. The carbon isotope effects in the cases of the doubly isotopically labelled CH3COCH(C2H5)(13CH2CH3) and CD3COCD(C2D5)(13CD2CD3) are 1.17 (±0.01) and 1.04 (±0.01), respectively. All of these isotope effects are consistent with a stepwise mechanism in which more than one step is rate determining.

  DOI：

  10.1002/oms.1210270319