ethyl 5-isopropyl-1-phenyl-1H-pyrazole-3-carboxylate | 1020724-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-isopropyl-1-phenyl-1H-pyrazole-3-carboxylate
• 英文别名: 5-Isopropyl-1-phenylpyrazole-3-carboxylic acid ethyl ester；ethyl 1-phenyl-5-propan-2-ylpyrazole-3-carboxylate
• CAS: 1020724-05-3
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: FMQGGUJRFXMMRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-isopropyl-1-phenyl-1H-pyrazole-3-carboxylate 在 lithium aluminium tetrahydride 、 三溴化磷 、 三苯基膦 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-bromomethyl-5-isopropyl-1-phenyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis and diabetic neuropathic pain-alleviating effects of 2N-(pyrazol-3-yl)methylbenzo[d]isothiazole-1,1-dioxide derivatives

  摘要：

  A novel series of fused-benzensulfonamide 2-N-(pyrazol-3-yl)methylbenzoldlisothiazole-1,1-dioxide derivatives was designed and synthesized as metabolically stable T-type calcium channel inhibitors. Several compounds, 9, 10, and 17, displayed potent T-type channel inhibitory activity. Among them, compounds 10 and 17 showed good metabolic stability in human liver microsomes, and low hERG channel and CYP450 inhibition. Compound 10 exhibited diabetic neuropathic pain-alleviating effects in a streptozotocin-induced peripheral diabetic neuropathy (PDN) model. The maximum efficacy of compound 10, which was 3-fold more potent than gabapentin, was observed at 1 h after administration, and co administration of compound 10 with gabapentin showed a considerable synergic effect. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.008

文献信息

• Palladium-Catalyzed Chelation-Assisted Regioselective Oxidative Dehydrogenative Homocoupling/<i>Ortho</i>-Hydroxylation in <i>N</i>-Phenylpyrazoles
  作者：Harikrishna Batchu、Soumya Bhattacharyya、Ruchir Kant、Sanjay Batra

  DOI：10.1021/acs.joc.5b00733

  日期：2015.8.7

  A palladium-catalyzed pyrazole-directed regioselective oxidative C(sp2)-H functionalization of the N-phenyl ring in N-phenylpyrazoles to afford either a biaryl bis-pyrazole (via dehydrogenative homocoupling) or N-(o-hydroxyphenyl)pyrazole (via C-H oxygenation) or their mixture is described. The substitutions on the N-phenyl ring and the pyrazole ring and the dilution of the reaction medium with respect to the TFA/TFAA mixture (substrate concentration) have a remarkable influence on the outcome of the reaction. It was discovered that if the reactions were performed under highly dilute conditions (ca. 10 times) then N-(o-hydroxyphenyl)pyrazoles were the major or the sole products.