hydrazone of 2-decanone | 105232-57-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: hydrazone of 2-decanone
• 英文别名: 2-Decanone hydrazone；(Decan-2-ylidene)hydrazine；decan-2-ylidenehydrazine
• CAS: 105232-57-3
• 化学式: C₁₀H₂₂N₂
• 分子量: 170.298
• InChiKey: CLXNUECSNSPDEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hydrazone of 2-decanone 在 lithium aluminium tetrahydride 、 iodine monofluoride 作用下， 生成 2,2-Difluorodecane
  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

文献信息

• Catalytic cycloaddition of diazoalkanes to fullerene C60
  作者：A. R. Tuktarov、V. V. Korolev、D. Sh. Sabirov、U. M. Dzhemilev

  DOI：10.1134/s1070428011010039

  日期：2011.1

  monosubstituted diazomethanes generated in situ by oxidation of aldehyde hydrazones in the presence of Pd(acac)2-2 PPh3-4 Et3Al as catalytic system resulted in selective formation of homofullerenes in which the alkyl substituent is located above the plane of the five-membered ring in C60. Under analogous conditions, unsymmetrical disubstituted diazomethanes generated from the corresponding ketone hydrazones gave

  在作为催化体系的Pd（acac）2 -2 PPh 3 -4 Et 3 Al的存在下通过醛oxidation酮的氧化原位生成的单取代重氮甲烷在富勒烯C 60上的环加成反应导致选择性形成高富勒烯，其中烷基取代基位于其中在C 60中五元环的平面之上。在类似条件下，由相应的酮生成的不对称二取代重氮甲烷产生了立体异构的5,6-开口加合物的混合物。
• A novel transformation of a carbonyl to a CF2 group
  作者：Shlomo Rozen、Michael Brand、Dov Zamir

  DOI：10.1021/ja00237a043

  日期：1987.2
• Conversion of the carbonyl group to CF2 using iodine monofluoride (IF)
  作者：Shlomo Rozen、Dov Zamir

  DOI：10.1021/jo00015a024

  日期：1991.7

  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.