2-[4-(benzyloxy)phenyl]-5-methyl-2,4-dihydropyrazol-3-one | 374924-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[4-(benzyloxy)phenyl]-5-methyl-2,4-dihydropyrazol-3-one
• 英文别名: 3-methyl-1-(4-benzyloxyphenyl)-2-pyrazolin-5-one；1-(4-Benzyloxyphenyl)-3-methyl-3-pyrazolin-5-one；5-methyl-2-(4-phenylmethoxyphenyl)-4H-pyrazol-3-one
• CAS: 374924-83-1
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: WXQKOFLHWYHKCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(benzyloxy)phenyl]-5-methyl-2,4-dihydropyrazol-3-one 在 五甲基苯 、 碳酸氢钠 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l
• 作为产物：
  描述：

  4-苯甲氧基苯胺盐酸盐 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 反应 25.17h， 生成 2-[4-(benzyloxy)phenyl]-5-methyl-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l

文献信息

• Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
  作者：Yong Yuan、Liang-Sen Li、Lin Zhang、Feng Wang、Lin Jiang、Lin Zuo、Qi Wang、Jian-Guo Hu、Aiwen Lei

  DOI：10.1039/d1cc00486g

  日期：——

  An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product

  已经开发了2.5-取代的吡唑啉-5-酮与硫氰酸铵之间的电化学氧化交叉偶联反应，从而在金属催化剂，外源氧化剂和外源电解质-的作用下产生了一系列前所未有的交叉偶联产物。免费条件。值得注意的是，由于所得的交叉偶联产物几乎不溶于MeCN，因此无需硅胶柱纯化即可提供纯产物。此外，制备的氧化铵是用于合成官能化吡唑衍生物的通用构建基。
• Highly Stereoselective Assembly of Polycyclic Molecules from 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation
  作者：Heng Lu、Zhoulong Fan、Chaodong Xiong、Ao Zhang

  DOI：10.1021/acs.orglett.8b01099

  日期：2018.5.18

  An Rh(III)-catalyzed C–H activation of pyrazolones with 1,6-enynes was investigated. The regioselectivity of the C–H activation/alkyne insertion is readily solved by using symmetric enyne coupling partners, and a C–H activation-triggered cascade reaction is realized, which involves alkyne insertion, tautomerization, and double cyclization to offer a class of structurally complex polycyclic architectures

  研究了Rh（III）催化吡唑啉酮与1，6-烯炔的C–H活化。通过使用对称的烯炔偶合剂可轻松解决C–H激活/炔烃插入的区域选择性，并实现了C–H激活触发的级联反应，其中涉及炔烃插入，互变异构和双环化，从而提供了一类结构复杂的多环架构。这种级联反应可在高区域选择性和立体专一性上耐受广泛的底物范围，并在一次操作中提供三个新的化学键和四个手性中心。进行了多环支架的各种衍生化，为产物提供了足够的空间用于进一步的功能转化。
• Rh(III)-Catalyzed Intermolecular C–H Amination of 1-Aryl-1<i>H</i>-pyrazol-5(4<i>H</i>)-ones with Alkylamines
  作者：Kui Wu、Zhoulong Fan、Yu Xue、Qizheng Yao、Ao Zhang

  DOI：10.1021/ol402965d

  日期：2014.1.3

  rhodium(III)-catalyzed intermolecular aromatic C–H amination directed by an intrinsic functionality of the substrate/product but also features aminating an existing drug with either primary or secondary N-benzoate alkylamines as the coupling partners.

  在温和的反应条件下，使用较低的催化剂负载量和广泛的胺化试剂，可以实现1-芳基-1 H-吡唑-5（4 H）-ones的分子间CH胺化反应。该方案不仅提供了以底物/产品的固有功能为导向的铑（III）催化的分子间芳族CH-H胺化反应的第一个实例，而且还提供了将现有药物与伯或仲N-苯甲酸酯烷基胺作为偶联剂进行胺化的功能。伙伴。