4-(diethylamino)-<2-13C>-2-butanone | 157686-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(diethylamino)-<2-13C>-2-butanone
• 英文别名: 2-¹³C-4-diethylamino-2-butanone；4-(diethylamino)-[2-13C]-2-butanone；4-(diethylamino)(213C)butan-2-one
• CAS: 157686-87-8
• 化学式: C₈H₁₇NO
• 分子量: 144.218
• InChiKey: XLEOCTUCGZANAC-VJJZLTLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  10.0
• 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：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(diethylamino)-<2-13C>-2-butanone 、 碘甲烷 反应 4.0h， 生成 2-¹³C-4-diethylamino-2-butanone methiodide
  参考文献：
  名称：

  4,4-Diphenylcyclohexa-2,5-dienylidene:  Rearrangement via an Isobenzene Pathway

  摘要：

  Pyrolytic decompostition of the Li salt of the tosylhydrazone of 4,4-diphenyl-2,5-cyclohexadienone produces a mixture of products which includes biphenyl, p-terphenyl, the azine of 4,4-diphenyl-2,5-cyclohexadienone, and o-terphenyl. C-13 labeling studies and computational results (semiempirical AM1 and density functional B3LYP/6-31G* molecular orbital calculations) elucidate the mechanistic pathway for the formation of o-terphenyl. A single mechanism is involved which proceeds through formation of an isobenzene species followed by subsequent phenyl and hydrogen migrations.

  DOI：

  10.1021/jo982400z
• 作为产物：
  描述：

  二碘甲烷 、 丙酮-2-13C 、 二乙胺 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 4-(diethylamino)-<2-13C>-2-butanone
  参考文献：
  名称：

  Novel DMPO-Derived 13C-Labeled Spin Traps Yield Identifiable Stable Nitroxides

  摘要：

  The nitrone 5,5-dimethyl-1-pyrroline N-oxide (DMPO) is the most common spin trap used for studying free radicals, yet its spin adducts are rapidly and irreversibly destroyed by cells. A methyl substitution at the 2-position of DMPO results in the nitrone 2,5,5-trimethyl-1-pyrroline N-oxide (M(3)PO). Radical addition to M(3)PO is expected to produce stable spin adducts; however, they have almost the same N hyperfine splitting (hfs), and, in the absence of a beta-hydrogen, different adducts are not distinguishable. To overcome this limitation, the synthesis of M(3)PO labeled with C-13 at the nitronyl (C-2) or the 2-methyl (alpha or beta to the aminoxyl group in the spin abduct, respectively) has been undertaken. [alpha-C-13]M(3)PO was synthesized from [2-C-13]acetone in a three-step pathway while [beta-C-13]M(3)PO was obtained from DMPO and [C-13]iodomethane. For M(3)PO, the nuclear magnetic moment of C-13 replaces that of the beta-hydrogen of DMPO and provides the additional hfs necessary for spin adduct identification. Primary radicals, such as *CH3, *CO2- and *OH were generated radiolytically, sonolytically, or enzymatically, trapped by [C-13]M(3)PO, and gave rise to nitroxide spin adducts which were identified and their magnetic parameters determined. The [C-13]M(3)PO spin adducts were far more stable than those of DMPO. Moreover, they were less susceptible to cellular-induced destruction. However, the superoxide adduct of M(3)PO was unstable and did not persist.

  DOI：

  10.1021/ja00095a040