3-甲基-1-(苯基甲基)-1H-吲唑 | 128364-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-甲基-1-(苯基甲基)-1H-吲唑
• 中文别名: 2-(4-氯苯甲酰基)环己酮
• 英文名称: 1-benzyl-3-methyl-1H-indazole
• 英文别名: 1-benzyl-3-methylindazole
• CAS: 128364-67-0
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: LZTZFGBSJUIHRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  385.7±21.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  3-甲基-1-(苯基甲基)-1H-吲唑 、 碘甲烷 生成 1-benzyl-2,3-dimethyl-indazolium; iodide
  参考文献：
  名称：

  v. Auwers; Lohr, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 108, p. 314

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Benzyl-N'-[1-(2-bromo-phenyl)-eth-(Z)-ylidene]-hydrazine 在 lead(IV) acetate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 3-甲基-1-(苯基甲基)-1H-吲唑
  参考文献：
  名称：

  Facile 5-endo ring closures to the azo group. A free radical synthesis of indazoles

  摘要：

  通过在苯中将1-(2-溴苯基)-1-甲氧基-1-(2-烷基偶氮基)乙烷与三正丁基锡和AIBN在80°C下处理，制备了五种1-烷基-3-甲基吲唑。在自由基环化步骤中，产率在39%到92%之间。类似的方法制备了1-苯基-3-甲基吲唑，但产率非常低（<5%）。通过自由基时钟方法估计，5-内环自由基闭合的速率常数为5.2×10^9 s^(-1)和9.2×10^8 s^(-1)。芳基自由基对C—C双键的类似5-内环化速率常数要比对偶氮基团的环化速率常数小得多。关键词：环化，自由基；偶氮基，自由基闭合；吲唑，自由基合成。

  DOI：

  10.1139/v90-088

文献信息

• Synthesis, structure and N–N bonding character of 1,1-disubstituted indazolium hexafluorophosphate
  作者：Yingtang Ning、Masatoshi Kawahata、Kentaro Yamaguchi、Yuko Otani、Tomohiko Ohwada

  DOI：10.1039/c8cc00183a

  日期：——

  conditions. The crystal structures were determined and are consistent with the presence of a stable N–N bond, which can be cleaved by hydrogenation. Both experimental and computational studies suggest a covalent bonding character of the N–N bond, with diminished aromaticity of the newly formed pyrazolium ring due to the quaternary ammonium atom (N1), in contrast to the aromatic character of the parent

  通过分子内亲电胺化反应在温和的条件下合成了1,1-二取代的吲哚鎓六氟磷酸盐。确定了晶体结构，并与存在稳定的N–N键相一致，该键可以通过氢化作用裂解。实验和计算研究均表明，N–N键具有共价键特征，而由于季铵原子（N1）而使新形成的吡唑环的芳香性降低，而母体吲唑则具有芳香性。
• MANUFACTURING PROCESS FOR NO-DONATING COMPOUNDS SUCH AS NO-DONATING DICLOFENAC
  申请人：ANDERSSON Johan

  公开号：US20090170934A1

  公开（公告）日：2009-07-02

  The present invention relates to a new process for the preparation of NO-donating compounds using a sulfonated intermediate. The invention relates to new intermediates prepared therein suitable for large scale manufacturing of NO-donating compounds. The invention further relates to the use of the new intermediates for the manufacturing of pharmaceutically active NO-donating compounds. The invention further relates to a substantially crystalline form of NO-donating NSAIDs, especially 2-[2-(nitrooxy)ethoxy]ethyl 2-[(2,6-dichlorophenyl)amino]phenyl}acetate, the preparation thereof and to pharmaceutical formulations containing said crystalline form and to the use of said crystalline form in the preparation of a medicament.

  本发明涉及一种使用磺化中间体制备NO供体化合物的新工艺。该发明涉及其中制备的适用于NO供体化合物大规模生产的新中间体。本发明还涉及使用新中间体制造药用活性NO供体化合物。此外，本发明还涉及NO供体NSAIDs的实质晶体形式，特别是2-[2-(硝氧基)乙氧基]乙基2-[(2,6-二氯苯基)氨基]苯基}乙酸酯的制备，以及含有该晶体形式的制药配方和在制备药物时使用该晶体形式的用途。
• Compounds
  申请人：MISSION THERAPEUTICS LIMITED

  公开号：US11130748B2

  公开（公告）日：2021-09-28

  The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 30 or Ubiquitin Specific Peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of conditions involving mitochondrial dysfunction and cancer. Compounds of the invention include compounds having the formula (I): (I) or a pharmaceutically acceptable salt thereof, wherein R1a, R1b, R1c, R1d, R1e, R1f, R1g, R2, X, L and A are as defined herein.

  本发明涉及新型化合物和制造去泛素化酶（DUB）抑制剂的方法。特别是，本发明涉及泛素 C 端水解酶 30 或泛素特异性肽酶 30（USP30）的抑制。本发明还涉及 DUB 抑制剂在治疗线粒体功能障碍和癌症方面的用途。本发明的化合物包括具有式（I）的化合物：(I)或其药学上可接受的盐，其中R1a、R1b、R1c、R1d、R1e、R1f、R1g、R2、X、L和A如本文所定义。
• Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
  作者：Zhen-Hua Li、Xiao-Meng Sun、Jin-Jing Qin、Zhi-Yong Tan、Wen-Biao Wang、Yao Ma

  DOI：10.1016/j.tet.2020.130945

  日期：2020.2

  An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N-N and N-C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope. (C) 2020 Elsevier Ltd. All rights reserved.
• A Scalable and Metal-Free Synthesis of Indazoles from 2-Aminophenones and In Situ Generated De-Boc-Protected <i>O</i>-Mesitylsulfonyl Hydroxylamine Derivatives
  作者：Jinlong Wang、Dongmin Shi、Zihao Wang、Fucai Ren、Xin Li、Yang’en You、Xinhua Liu、Yazhou Lou

  DOI：10.1021/acs.joc.3c01211

  日期：2023.9.15