3,5-二叔丁基-1-甲基吡唑 | 141665-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3,5-二叔丁基-1-甲基吡唑
• 英文名称: 1-methyl-3,5-di-tert-butylpyrazole
• 英文别名: 1-Methyl-3,5-di-t-butylpyrazole；3,5-ditert-butyl-1-methylpyrazole
• CAS: 141665-18-1
• 化学式: C₁₂H₂₂N₂
• 分子量: 194.32
• InChiKey: HOPUBWIABHRCKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 3,5-二叔丁基-1-甲基吡唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以76%的产率得到3,5-di-tert-butyl-1-((trimethylsilyl)methyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis and characterization of lithium, aluminium and zinc complexes supported by pyrazolyl-based N,N′-chelate ligands

  摘要：

  一系列含有 [3,5-R2C3HN2CHC(R1)N(R2)]− 配体的锂、铝和锌配合物被合成并表征。将 1-(Me3SiCH2)-3,5-R2C3HN2 (R = Me, But) 与 LiBun 反应，随后与 ButCN 反应，得到 [Li{N(SiMe3)C(But)CHN2C3HR2-3,5}]2（R = Me，2a；R = But，2b）。将 2a 和 2b 与 ZnCl2 反应，得到锌配合物 [Zn(Cl){N(SiMe3)C(But)CHN2C3HR2-3,5}]2（R = Me，3a；R = But，3b）。将 o-RC6H4NHC(Ph)CHN2C3HMe2-3,5（R = OPri，5a；R = Me，5b）与 LiBun 反应，得到类似于 2a 或 2b 的锂配合物，[Li{N(o-RC6H4)C(Ph)CHN2C3HMe2-3,5}]（R = OPri，6a；R = Me，6b）。将 6b 与 ZnCl2 反应，生成锌配合物 [Zn(Cl){N(o-MeC6H4)C(Ph)CHN2C3HMe2-3,5}]（7），与 AlCl3 反应，得到 [Al(Cl2){N(o-MeC6H4)C(Ph)CHN2C3HMe2-3,5}]（8）。将 5a 与 ZnEt2 反应，生成 [Zn{N(o-PriC6H4)C(Ph)CHN2C3HMe2-3,5}2]（9）。将 5a 和 5b 与 AlR′3（R′ = Me, Et）反应，得到铝配合物 [Al(R′2){N(o-RC6H4)C(Ph)CHN2C3HMe2-3,5}]（R = OPri，R′ = Me，10a；R = Me，R′ = Me，10b；R = OPri，R′ = Et，10c；R = Me，R′ = Et，10d）。在 5b 和 AlEt3 的反应产物中还分离出少量物种 [Al(Et2){N(o-MeC6H4)C(Ph)(Et)CH2N2C3HMe2-3,5}]（11）。所有新化合物都通过 1H 和 13C NMR 光谱和元素分析进行了表征。配合物 2a、8、10a、10d 和 11 的结构还通过单晶 X 射线衍射技术进行了表征。

  DOI：

  10.1039/b811094h
• 作为产物：
  描述：

  2,2,6,6-四甲基-3,5-庚二酮 、 甲基肼 以 乙醇 为溶剂， 以88%的产率得到3,5-二叔丁基-1-甲基吡唑
  参考文献：
  名称：

  Basicity of C-substituted pyrazoles in the gas phase: an experimental (ICR) and theoretical study

  摘要：

  The experimental gas-phase proton affinities (PAs) of 32 N-H and N-methyl pyrazoles have been determined by means of Fourier transform ion cyclotron resonance spectroscopy (FTICR). Together with the previously reported PAs for 12 C-methyl-substituted pyrazoles, they provide a set of 57 data (counting each tautomer separately). The remarkably large spread of PAs, ca. 55 kcal.mol-1, makes this set most suitable for structural analyses. In a few cases, ab initio 6-31G//6-31G protonation energies were calculated and found to be linearly related to the experimental PAs to a very high degree of precision. A simple additive model of substituent effects on PAs (including substitutions at positions 3, 4, and 5) was found to hold, even for very crowded derivatives such as 1,4-dimethyl-3,5-di-tert-butylpyrazole (27). The only significant interaction appears between phenyl groups at positions 3 and 5. The statistically averaged substituent effects on PAs were successfully analyzed in terms of polarizability and field and resonance contributions, according to the Taft-Topsom model. Both positions 3 and 5 behave in a way similar to that of position 2 in the pyridines. From this interesting result it follows that, with the exception of 3-aminopyrazole, the tautomerism of pyrazoles is not very dependent of the nature of the 3(5)-substituent.

  DOI：

  10.1021/jo00040a040

文献信息

• Hepatitis C Virus Inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US20130183269A1

  公开（公告）日：2013-07-18

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组成物，以及抑制NS5A蛋白功能的方法。
• [EN] 6-HETEROARYLOXY BENZIMIDAZOLES AND AZABENZIMIDAZOLES AS JAK2 INHIBITORS<br/>[FR] 6-HÉTÉROARYLOXY BENZIMIDAZOLES ET AZABENZIMIDAZOLES EN TANT QU'INHIBITEURS DE JAK2
  申请人：AJAX THERAPEUTICS INC

  公开号：WO2021226261A1

  公开（公告）日：2021-11-11

  The present disclosure provides 6-heteroaryloxy benzimidazole and azabenzimidazole compounds and compositions thereof useful for inhibiting JAK2.

  本公开提供了6-杂芳氧基苯并咪唑和氮杂苯并咪唑化合物及其组合物，用于抑制JAK2。
• METHODS OF TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES BASED ON APOE4 GENOTYPE
  申请人：T3D Therapeutics, Inc.

  公开号：US20180153859A1

  公开（公告）日：2018-06-07

  The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders based on the ApoE4 genotype of human subjects.

  本发明提供了关于人类主体的ApoE4基因型的吲哌乙酸及其衍生物的治疗和/或预防认知障碍的方法。
• METHODS OF DOSE ADMINISTRATION FOR TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES
  申请人：T3D Therapeutics, Inc.

  公开号：US20180153860A1

  公开（公告）日：2018-06-07

  The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders.

  本发明提供了茚乙酸及其衍生物，以及用于治疗和/或预防认知障碍的方法。
• METHOD OF TREATING CONTRAST-INDUCED NEPHROPATHY
  申请人：FOO Shi Yin

  公开号：US20120122844A1

  公开（公告）日：2012-05-17

  The present invention provides the use of a neutral endopeptidase inhibitor, in the manufacture of a medicament for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The invention also relates to the use of a compound of Formula I: wherein R 1 , R 2 , R 3 , R 5 , X, A 3 , B 1 , s and n are defined herein, for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The present invention further provides a combination of pharmacologically active agents for use in the treatment, amelioration and/or prevention of contrast-induced nephropathy.

  本发明提供了中性内切肽酶抑制剂的使用，用于制造用于治疗、改善和/或预防造影剂诱导性肾病的药物。该发明还涉及使用化合物Formula I中的化合物：其中R1、R2、R3、R5、X、A3、B1、s和n在此处定义，用于治疗、改善和/或预防造影剂诱导性肾病。本发明进一步提供了用于治疗、改善和/或预防造影剂诱导性肾病的药理活性剂的组合。