<2H>Methyl neopentyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <2H>Methyl neopentyl ketone
• 英文别名: 1-Deuterio-4,4-dimethylpentan-2-one
• 化学式: C₇H₁₄O
• 分子量: 115.18
• InChiKey: AZASWMGVGQEVCS-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁酰氯 在 重水 、 三正丁基氢锡 、 反式-二叔丁基连二次硝酸酯 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 <2H>Methyl neopentyl ketone
  参考文献：
  名称：

  Radical addition to carbenoids. Chain reactions of α-diazo carbonyl compounds with triorganotin hydrides, tris(trimethylsilyl)silane and allyltributylstannane

  摘要：

  alpha-Diazo ketones RC(O)CH=N-2 react with tributyltin hydride at 60 degrees C in benzene to give the corresponding alpha-stannyl ketones RC(O)CH(2)SnBu(3), which exist in equilibrium with the stannyl enol ether tautomers R(Bu(3)SnO)C=CH2. The reactions are initiated by di-tert-butyl hyponitrite and follow a free-radical chain mechanism, Triphenyltin hydride and tris(trimethylsilyl)silane [(TMS)(3)SiH] react similarly, the latter to yield the alpha-silyl ketone RC(O)CH2Si(TMS)(3) which does not isomerise to the more stable silyl enol ether R[(TMS)(3)SiO]C=CH2 under the reaction conditions. This result indicates that TMS(3)Si reacts at the alpha-carbon atom of the alpha-diazo ketone to give R(CO)CHSiTMS(3), probably via an initial diazenyl radical adduct; triorganotin radicals are assumed to react in the same way, When the group R in the alpha-diazo ketone is but-3-enyl, the intermediate alpha-metalloalkyl radical undergoes 5-exo-cyclisation. Aliyltributylstannane reacts with a-diazo ketones and with ethyl alpha-diazoacetate in refluxing benzene, in the presence of 2,2'-azo(2-methylpropionitrile) as initiator, to give butenyl ketones RC(O)CH2CH2CH=CH2 and ethyl pent-4-enoate, respectively, after a hydrolytic work-up.

  DOI：

  10.1039/p19960000769