4-hexyloxybenzylhydrazone | 1353288-23-9

• 英文名称: 4-hexyloxybenzylhydrazone
• 英文别名: (4-Hexoxyphenyl)methylidenehydrazine；(4-hexoxyphenyl)methylidenehydrazine
• CAS: 1353288-23-9
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: PULLXMCFWFSODK-UHFFFAOYSA-N

物化性质

• 沸点：
  351.424±44.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.999±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hexyloxybenzylhydrazone 、 4-己氧基-2-羟基苯甲醛 在 溶剂黄146 作用下， 反应 6.0h， 以75%的产率得到N-[4-(hexyloxy)-2-hydroxybenzylidene]-N'-(4-hexyloxybenzylidene) azine
  参考文献：
  名称：

  Synthesis, Characterization and Mesomorphic Properties of Unsymmetrical N-[4-(Alkoxy)-2-Hydroxybenzylidene]-N′-(4-Alkoxybenzylidene) Azines and Their Copper (II) Complexes

  摘要：

  A new series of mesogenic unsymmetrical azines, N-[4-(alkoxy)-2-hydroxybenzylidene]-N'-(4-n-alkoxybenzylidene) azines, ROC6H4CH=N-N=CHC6H3OHOR, where R = CmH2m+1 (m = 6, 8, 10, 12, and 14), and their copper (II) complexes has been synthesized. They were characterized by elemental analyses, Fourier transform infrared (FT-IR), H-1 and C-13 nuclear magnetic resonance (NMR) spectra, ultraviolet (UV)-visible, and magnetic susceptibility measurements. The copper (II) complexes are square planar. The mesomorphic properties of these compounds were investigated by differential scanning calorimetry and polarizing microscopy. The unsymmetrical azines with m = 6, 12, and 14 exhibit monotropic nematic, enantiotropic, and monotropic smectic A phases, whereas azines with m = 8 display enantiotropic nematic and m = 10 display both enantiotropic smectic A and nematic mesophases in the heating and cooling cycles. The copper (II) complexes of the azines are nonmesomorphic in nature with high clearing temperatures and displayed polymorphism (crystal-crystal transitions) in both the heating and cooling cycles.

  DOI：

  10.1080/15421406.2011.607323
• 作为产物：
  描述：

  溴己烷 在 potassium carbonate 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-hexyloxybenzylhydrazone
  参考文献：
  名称：

  Synthesis, Characterization and Mesomorphic Properties of Unsymmetrical N-[4-(Alkoxy)-2-Hydroxybenzylidene]-N′-(4-Alkoxybenzylidene) Azines and Their Copper (II) Complexes

  摘要：

  A new series of mesogenic unsymmetrical azines, N-[4-(alkoxy)-2-hydroxybenzylidene]-N'-(4-n-alkoxybenzylidene) azines, ROC6H4CH=N-N=CHC6H3OHOR, where R = CmH2m+1 (m = 6, 8, 10, 12, and 14), and their copper (II) complexes has been synthesized. They were characterized by elemental analyses, Fourier transform infrared (FT-IR), H-1 and C-13 nuclear magnetic resonance (NMR) spectra, ultraviolet (UV)-visible, and magnetic susceptibility measurements. The copper (II) complexes are square planar. The mesomorphic properties of these compounds were investigated by differential scanning calorimetry and polarizing microscopy. The unsymmetrical azines with m = 6, 12, and 14 exhibit monotropic nematic, enantiotropic, and monotropic smectic A phases, whereas azines with m = 8 display enantiotropic nematic and m = 10 display both enantiotropic smectic A and nematic mesophases in the heating and cooling cycles. The copper (II) complexes of the azines are nonmesomorphic in nature with high clearing temperatures and displayed polymorphism (crystal-crystal transitions) in both the heating and cooling cycles.

  DOI：

  10.1080/15421406.2011.607323

文献信息

• Anti-Markovnikov Hydroalkylation of Styrene Derivatives via Hydrazones Catalyzed by Ru-PNP Complex
  作者：Siyi Luo、Hanh D. M. Pham、Chen-Chen Li、Zihang Qiu、Ruofei Cheng、Rustam Z. Khaliullin、Chao-Jun Li

  DOI：10.1021/acs.orglett.4c00610

  日期：2024.4.19

  Ru(II)-PNP complex demonstrated high activity in the anti-Markovnikov hydroalkylation of nonpolarized terminal alkenes via hydrazones. Hydrazone served as a carbanion equivalent to combine with the electrophilic alkene substrate upon activation by the ruthenium catalyst, forming a new C–C bond in a concerted pathway with N2 as the only theoretical byproduct. Experimental and computational studies suggested

  结构明确的 Ru(II)-PNP 配合物在非极化末端烯烃通过腙的反马尔可夫尼科夫加氢烷基化中表现出高活性。腙充当碳负离子，在钌催化剂的活化下与亲电子烯烃底物结合，在协同途径中形成新的C-C键，N 2作为唯一的理论副产物。实验和计算研究表明存在推拉相互作用，激活烯烃进行腙加成，然后推断出其机理。