tert-butyl-(2,2-dimethyl-propionyl)-ketene | 67832-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-(2,2-dimethyl-propionyl)-ketene
• 英文别名: 2-tert-butyl-4,4-dimethyl-pent-1-ene-1,3-dione；InChI=1/C11H18O2/c1-10(2,3)8(7-12)9(13)11(4,5)6/h1-6H
• CAS: 67832-67-1
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KNLIHMYYNUZKLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  39-41 °C(Press: 0.75 Torr)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl-(2,2-dimethyl-propionyl)-ketene 在 水 作用下， 以 乙腈 为溶剂， 生成 (E)-2-tert-butyl-3-hydroxy-4,4-dimethylpent-2-enoic acid
  参考文献：
  名称：

  The unusual hydration reactivity of acylketenes: Theoretical and experimental studies

  摘要：

  Ab initio MO calculations indicate that the hydration of acylketenes may be assisted by complexation of the nucleophilic H2O molecule to the oxygen of the acyl substituent. Experimental studies for hydration of EtO2CC(Bu-t)=C=O (4) support this pathway.

  DOI：

  10.1016/s0040-4039(00)77499-5
• 作为产物：
  描述：

  4-diazo-2,2,6,6-tetramethylheptane-3,5-dione 以 solid matrix 为溶剂， 反应 0.17h， 生成 tert-butyl-(2,2-dimethyl-propionyl)-ketene
  参考文献：
  名称：

  Direct observation of .alpha.-oxo ketenes from the photolysis of .alpha.-diazo .beta.-diketones

  摘要：

  Monitoring by IR spectroscopy of the broad-band irradiation of the symmetrically substituted 2-diazo-cyclohexane-1,3-dione (I 1), 3-diazopentane-2,4-dione (19), and 4-diazo-2,2,6,6-tetramethylheptane-3,5-dione (24) in Ar matrices at 12 K showed the formation of 2-carbonylcyclopentanone (s-Z-12), acetyl(methyl)ketene (s-E-20), and tert-butyl(pivaloyl)ketene (s-E-25), respectively, in less than 10 min. On increasing the photolysis time to >3 h, the alpha-oxo ketenes 12,20, and 25 decarbonylated to the corresponding oxocarbenes which underwent Wolff rearrangement to carbonylcyclobutane (15), dimethylketene (23), and di-tert-butylketene (28), respectively. The reaction of 2-carbonylcyclopentanone (12) with CH3OH was monitored by IR spectroscopy. Thus, it was found that the reaction started at ca. 100 K and was essentially complete at 140 K, involving the initial formation of the enol form (9) of methyl 2-oxocyclopentanecarboxylate.

  DOI：

  10.1021/jo00044a019

文献信息

• Wolff, Steven; Agosta, William C., Canadian Journal of Chemistry, 1984, vol. 62, p. 2429 - 2434
  作者：Wolff, Steven、Agosta, William C.

  DOI：——

  日期：——
• Direct observation of .alpha.-oxo ketenes formed from 1,3-dioxin-4-ones and the enols of .beta.-keto esters
  作者：Beat Freiermuth、Curt Wentrup

  DOI：10.1021/jo00007a008

  日期：1991.3

  The enol forms of beta-keto esters thermolyze to alcohols and alpha-oxo ketenes, which are characterized by low-temperature IR spectroscopy and on warming regenerate the beta-hydroxy-alpha,beta-unsaturated esters. The matrix isolated s-Z and s-E forms of alpha-oxo ketenes are characterized and photochemically converted into other conformers or sites. Matrix photolysis of 2,2,6-trimethyl-1,3-dioxin-4-one gives the s-Z acetylketene initially. Alpha-Oxo ketenes polymerize in the cold and dimerize only at elevated temperatures.
• Nikolaev,V.A. et al., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 1338 - 1346
  作者：Nikolaev,V.A. et al.

  DOI：——

  日期：——
• FREIERMUTH, BEAT;WENTRUP, CURT, J. ORG. CHEM., 56,(1991) N, C. 2286-2289
  作者：FREIERMUTH, BEAT、WENTRUP, CURT

  DOI：——

  日期：——
• WOLFF, S.;AGOSTA, W. C., CAN. J. CHEM., 1984, 62, N 11, 2429-2434
  作者：WOLFF, S.、AGOSTA, W. C.

  DOI：——

  日期：——

表征谱图