Phenyl-aceton-methylhydrazon | 16602-83-8

• 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: Phenyl-aceton-methylhydrazon
• 英文别名: Phenylaceton-N-methylhydrazon；phenyl-acetone-methylhydrazone；N-(1-phenylpropan-2-ylideneamino)methanamine
• CAS: 16602-83-8
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: SWCMAMVWQSTWFT-UHFFFAOYSA-N

物化性质

• 沸点：
  258.7±33.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Phenyl-aceton-methylhydrazon 在 三正丁基氢锡 、 iodine monofluoride 作用下， 生成 2,2-二氟丙基苯
  参考文献：
  名称：

  Conversion of the carbonyl group to CF2 using iodine monofluoride (IF)

  摘要：

  A novel method for the transformation of CO --> CF2 is described. The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements. Various hydrazones have been examined and compared with each other. Unsubstituted ones are usually the most suitable although they are not always easy to purify and store. N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results. The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower. Oximes could also be successfully reacted. The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the alpha-iododifluoro derivatives. The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.

  DOI：

  10.1021/jo00015a024
• 作为产物：
  描述：

  甲基肼 、 苯基丙酮 以 苯 为溶剂， 反应 2.0h， 生成 Phenyl-aceton-methylhydrazon
  参考文献：
  名称：

  N-alkenyl-3,5-pyrazolidinediones from ketone hydrazones, PCl3 and malonic acid

  摘要：

  The title compounds 3, a new series of 3,5-pyrazolidinediones, have been synthesized at room temperature by a one-pot reaction between ketone hydrazone 1, PCl3 and malonic acid. Changing the order of addition of reagents, or their simultaneous addition, gave identical results. In all me procedures the yields are good and in the cases a,b,c and g the E-alkenyl isomer was obtained as the exclusive isomer. A dual mechanism which depends on the order of addition of the reactants is hypothesised.

  DOI：

  10.1016/0040-4020(95)00550-r

文献信息

• An efficient procedure for the synthesis of N-alkenyl derivatives of six-membered and larger 1,2-diaza heterocycles
  作者：Graziano Baccolini、Athanase Munyaneza、Carla Boga

  DOI：10.1016/0040-4020(96)00821-6

  日期：1996.10

  The use of diazaphosphole derivatives generated in situ or the PCl3/hydrazone combination can be applied in a novel efficient one-pot procedure for the synthesis at room temperature of the title six-, seven- and eight-membered rings using always high concentration of the reagents (0.2–0.5M). N-alkenyl derivatives of 1,2-diazaheterocycles such as 8 (perhydro-pyridazine-3,6-diones), 9 (perhydro-1,2-diazepin-3

  可以以新颖高效的一锅法应用原位生成的二氮磷腈衍生物或PCl 3 / hydr组合物在室温下合成标题六元，七元和八元环，并且始终使用高浓度的二氮杂磷衍生物。试剂（0.2–0.5M）。1,2-二氮杂杂环的N-烯基衍生物，例如8（全氢哒嗪-3,6-二酮），9（全氢1,2-二氮杂3,7-二酮），10（全氢1,2-二酮）通过PCl 3的反应获得重氮3,8-二酮和11（1,2-二氢哒嗪-3,6-二酮），酮甲基hydr和琥珀酸，戊二酸，己二酸和马来酸。改变试剂的添加顺序或同时添加试剂的结果相同。在所有程序中，收率均良好。总是观察到E异构体的排他或普遍形成。由对通过E异构体异构化获得的E，Z混合物进行的一些NOE实验推导出环外双键的E-构型。还提出了反应机理。
• Synthesis of pyrroles under mild conditions using PCl3, ketones, and alkylhydrazines
  作者：Graziano Baccolini、Claudio Sandali

  DOI：10.1039/c39870000788

  日期：——

  A one-pot synthesis of symmetrical pyrroles was obtained by reaction of alkylhydrazones of enolizable ketones, PCl3, and subsequent addition of the same ketone.

  通过可烯醇化的酮的烷基en PCl 3的反应，然后添加相同的酮，可以一锅合成对称的吡咯。
• Central Stimulants. Chemistry and Structure-Activity Relationship of Aralkyl Hydrazines
  作者：John H. Biel、Alexander E. Drukker、Thomas F. Mitchell、Edwin P. Sprengeler、Patrick A. Nuhfer、Alvin C. Conway、A. Horita

  DOI：10.1021/ja01520a048

  日期：1959.6
• Baccolini, Graziano, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1053 - 1056
  作者：Baccolini, Graziano

  DOI：——

  日期：——
• Synthesis of 2-alkenylpyrazol-3(2H)-one derivatives under mild conditions
  作者：Graziano Baccolini、Daniele Evangelist、Corrado Rizzoli、Paolo Sgarabotto

  DOI：10.1039/p19920001729

  日期：——

  The title compounds have been synthesized by a one-pot two-stage reaction of PCI,, ketone methyl-hydrazones and methyl acetoacetate. Both stages were carried out at room temperature and the corresponding 2-alkenyl-1,5-dimethylpyrazol-3(2H)-ones 5, which are an unknown series of pyrazolones, were obtained in good yields. Use of a variety of enolizable ketones has shown that the reaction always occurs with the predominance of the (E)-isomer. X-Ray structure determinations of an (E)- and a (Z)-derivative [(E)-5c.HCl and (Z)-5b] permitted the assignment of their structures. The aromaticity of these derivatives is discussed.