p-Methylbenzylmethylketonoxim | 114306-23-9

• 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: p-Methylbenzylmethylketonoxim
• 英文别名: 1-(4-methylphenyl)propan-2-one oxime；1-(4-Methyl-phenyl)-propan-2-on-oxim；1-(p-methylphenyl)-2-propanone oxime；p-tolyl-acetone oxime；p-Tolyl-aceton-oxim；N-[1-(4-methylphenyl)propan-2-ylidene]hydroxylamine
• CAS: 114306-23-9
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: QENZFBIAQUGNPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  90 °C
• 沸点：
  302.8±21.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-Methylbenzylmethylketonoxim 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 DL-2-Hydroxylamino-1-(4-methyl-phenyl)-propan
  参考文献：
  名称：

  N-烷基羟乙二酰胺及其邻甲基醚的行为和神经药理作用。

  摘要：

  DOI：

  10.1021/jm00325a020
• 作为产物：
  描述：

  4-甲基苯丙酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以53%的产率得到p-Methylbenzylmethylketonoxim
  参考文献：
  名称：

  贝克曼反应中的动态路径分叉：动力学分析的支持

  摘要：

  当迁移基团具有合理的阳离子稳定性时，肟与酰胺的反应（称为贝克曼重排）可能发生断裂，形成碳正离子+腈。CH 3 CN水溶液中1-取代苯基-2-丙酮酮衍生物（7 -X）和相关底物（8 -X，9a -X）的肟磺酸盐的反应既产生了重排产物（酰胺）又产生了裂解产物（醇） ），其比例取决于系统；7 -X的反应主要产生酰胺，而9a -X的主要产物为醇。日志k –log k系统之间的曲线给出了极好的线性相关性，其斜率接近于1。结果支持贝克曼重排/片段化反应的速率确定TS后路径分支的发生，这是先前在分子动力学模拟的基础上提出的。得出的结论是，路径分叉现象可能比想像的更为普遍，并且基于传统TS理论的反应性-选择性论点甚至可能并不总是适用于即使是著名的教科书有机反应。

  DOI：

  10.1021/jo200728t

文献信息

• Controllable Synthesis of Mesoporous Iron Oxide Nanoparticle Assemblies for Chemoselective Catalytic Reduction of Nitroarenes
  作者：Ioannis T. Papadas、Stella Fountoulaki、Ioannis N. Lykakis、Gerasimos S. Armatas

  DOI：10.1002/chem.201504685

  日期：2016.3.18

  electronics to magnetism, and catalysis. Recent efforts have targeted new nanostructured forms of Fe2O3 with high surface area‐to‐volume ratio and large pore volume. Herein, the synthesis of 3D mesoporous networks consisting of 4–5 nm γ‐Fe2O3 nanoparticles by a polymer‐assisted aggregating self‐assembly method is reported. Iron oxide assemblies obtained from the hybrid networks after heat treatment have

  氧化铁（III）是一种低成本材料，其应用范围从电子学到磁学和催化学。最近的工作针对具有高表面积体积比和大孔体积的新型纳米结构Fe 2 O 3。在此，由4-5纳米γ -铁的三维中孔网络的合成2 ö 3报道由聚合物辅助聚集自组装方法的纳米颗粒。热处理后从混合网络中获得的氧化铁组件具有开孔结构，具有高表面积（最大167 m 2  g -1）和均匀的孔（约6.3 nm）。构成氧化铁纳米晶体可以从经历可控相变了γ-Fe 2ø 3到的α-Fe 2 ö 3和成Fe 3 ö 4不同退火条件下，同时保持三维结构和开放的孔隙。这些新的集成结构显示出高催化活性和稳定性，即使在大规模合成中，也可以选择性地将芳基和烷基硝基化合物还原为相应的芳基胺和肟。
• Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
  作者：Rémi Lavernhe、Rubén O. Torres‐Ochoa、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202110901

  日期：2021.11.2

  AbstractNitrogen‐substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper‐catalyzed synthesis of ynimines from readily available O‐acetyl ketoximes and terminal alkynes. A wide range of O‐acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross‐coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.
• Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt, Chemische Berichte, 1981, vol. 114, # 12, p. 3813 - 3830
  作者：Langhals, Heinz、Range, Guenter、Wistuba, Eckehardt、Ruechardt, Christoph

  DOI：——

  日期：——
• Synthesis and monoamine transporter binding properties of 2β-[3′-(substituted benzyl)isoxazol-5-yl]- and 2β-[3′-methyl-4′-(substituted phenyl)isoxazol-5-yl]-3β-(substituted phenyl)tropanes
  作者：Chunyang Jin、Hernán A. Navarro、Kevin Page、F. Ivy Carroll

  DOI：10.1016/j.bmc.2008.05.073

  日期：2008.7

  A series of 2 beta-[3'-(substituted benzyl)isoxazol-5-yl]- and 2 beta-[3'-methyl-4'-(substituted phenyl)isoxazol-5- yl]-3 beta-(substituted phenyl)tropanes were prepared and evaluated for affinities at dopamine, serotonin, and norepinephrine transporters using competitive radioligand binding assays. The 2 beta-[3'-(substituted benzyl)isoxazol-5-yl]-3 beta-(substituted phenyl)tropanes (3a-h) showed high binding affinities for the dopamine transporter (DAT). The IC50 values ranged from 5.9 to 22 nM. On the other hand, the 2 beta-[3'-methyl- 4'-(substituted phenyl)isoxazol-5-yl]-3 beta-(substituted phenyl)tropanes (4a-h), with IC50 values ranging from 65 to 173 nM, were approximately 3- to 25-fold less potent than the corresponding 2 beta-[ 3'-(substituted benzyl)isoxazol] tropanes. All tested compounds were selective for the DAT relative to the norepinephrine transporter (NET) and serotonin transporter (5-HTT). 3 beta-(4-Methylphenyl)-2 beta-[3'-(4-fluorobenzyl)isoxazol-5-yl] tropane (3b) with IC50 of 5.9 nM at the DAT and K(i)s of 454 and 113 nM at the NET and 5-HTT, respectively, was the most potent and DAT-selective analog. Molecular modeling studies suggested that the rigid conformation of the isoxazole side chain in 4a-h might play an important role on their low DAT binding affinities. (c) 2008 Elsevier Ltd. All rights reserved.
• Jacobsen et al., Skandinavisches Archiv fur Physiologie, 1938, vol. 79, p. 258,280
  作者：Jacobsen et al.

  DOI：——

  日期：——