phenyliminopropadienone | 145355-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyliminopropadienone
• CAS: 145355-48-2
• 化学式: C₉H₅NO
• 分子量: 143.145
• InChiKey: QFSVTFOXCJWSGX-UHFFFAOYSA-N

物化性质

• 沸点：
  262.9±33.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-5--1,3-dioxane-4,6-dione 生成 phenyliminopropadienone
  参考文献：
  名称：

  Iminopropadienones, RNCCCO: syntheses and reactions

  摘要：

  苯亚氨丙二烯酮，PhNCCCO，被制备并表征，同时描述了初步的化学反应。

  DOI：

  10.1039/c39920001571

文献信息

• Aryliminopropadienone−<i>C</i>-Amidoketenimine− Amidinoketene−2-Aminoquinolone Cascades and the Ynamine−Isocyanate Reaction
  作者：Curt Wentrup、V. V. Ramana Rao、Wilhelm Frank、Belinda E. Fulloon、Daniel W. J. Moloney、Thomas Mosandl

  DOI：10.1021/jo982471y

  日期：1999.5.1

  and triazole 19 and are observed by IR spectroscopy. Ketenimine-3-carboxylic acid esters 12a are isolable at room temperature. Ketenes 11 and ketenimines 12 undergo rapid interconversion in the gas phase, and the ketenes cyclize to 4-quinolones 13. When using an amine leaving group in Meldrum's acid derivatives 9c, the major reaction products are aryliminopropadienones, ArN=C=C=C=O (15). The latter

  亚胺基酮烯11和氧杂环丁酮12是通过快速真空热解Meldrum的酸衍生物9，吡咯二酮17和18以及三唑19生成的，并通过红外光谱进行观察。Ketenimine-3-羧酸酯12a在室温下是可分离的。酮基11和酮亚胺12在气相中快速转变，并且酮烯环化为4-喹诺酮13。当在Meldrum的酸衍生物9c中使用胺离去基团时，主要反应产物是芳基丙二烯酮，ArN = C = C = C = O（15）。后者与1当量的亲核试剂反应生成酮亚胺12，并与2当量的反应生成丙二酰亚胺衍生物16.N-芳基酮亚胺-C-羧酰胺12c在25-40℃的温度下通过瞬态a基11c环化为喹诺酮13c。这意味着即使在室温下，烯酮和酮亚胺也可以通过二甲氨基的1，3-移位而快速相互转化。这种相互转换解释了先前对乙胺异氰酸酯反应的结果了解甚少。讨论了4-喹诺酮/ 4-喹啉醇互变异构的溶剂依赖性。NMe（2）小组在酰胺基亚胺12c和丙二酰胺和am
• Iminopropadienones, RN:C:C:C:O. Theory and experiment
  作者：T. Mosandl、S. Stadtmuller、M. Wah Wong、C. Wentrup

  DOI：10.1021/j100055a007

  日期：1994.1

  Ab initio molecular orbital calculations at the MP2/6-31G* level have been used to examine the structures and infrared spectra of a new class of compounds, the iminopropadienones, RN=C=C=C=O (R = H, CH3, and Ph). The agreement between calculated and experimental IR spectra of PhNCCCO, Ph(15)NCCCO, and PhNCC(13)CO is excellent. Inclusion of electron correlation is found to be important for the correct prediction of the relative intensities of the cumulenic stretching vibrations. All three iminopropadienones are predicted to have a slightly bent NCCCO backbone (angle CCC approximate to 176 degrees). As with carbon suboxide, these cumulenes are calculated to have an extremely flat CCC bending potential. The parent compound, HNCCCO (4a) is calculated to be thermodynamically stable toward dissociations into (i) HNCC + CO, (ii) HNC + CCO, (iii) HN + CCCO, and (iv) H. + NCCCO.. Rearrangement of 4a to the more stable cyanoketene isomer requires a sizeable barrier of 402 kJ mol(-1) [G2(MP2)]. The calculated stability of 4a is consistent with its experimental observation in neutralization-reionization mass spectrum. The adiabatic ionization energy and heat of formation of HNCCCO are predicted to be 9.51 eV and 175 kJ mol(-1), respectively.
• Kappe, C. Oliver; Flammang, Robert; Wentrup, Curt, Heterocycles, 1994, vol. 37, # 3, p. 1615 - 1622
  作者：Kappe, C. Oliver、Flammang, Robert、Wentrup, Curt

  DOI：——

  日期：——