2-(2-bromoethyl)-2H-indazole | 186667-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 2-(2-bromoethyl)-2H-indazole
• 英文别名: 2-(2-bromoethyl)indazole；2-(2-bromo-ethyl)-2H-indazole；2-(2-Brom-aethyl)-2H-indazol
• CAS: 186667-00-5
• 化学式: C₉H₉BrN₂
• 分子量: 225.088
• InChiKey: JMGKTQUKKXZIFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-(2-bromoethyl)-2H-indazole 在 sodium hydroxide 作用下， 反应 28.5h， 生成 N-2-(indazol-2-yl)ethyliminodiacetic acid sodium salt
  参考文献：
  名称：

  N-2-(Azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging

  摘要：

  The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T-1 and T-2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T-2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00273-9
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三溴化磷 作用下， 生成 2-(2-bromoethyl)-2H-indazole
  参考文献：
  名称：

  v. Auwers; Kleiner, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 118, p. 74,90

  摘要：

  DOI：

文献信息

• Synthesis of Annulated 2<i>H</i>-Indazoles and 1,2,3- and 1,2,4-Triazoles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Reaction
  作者：Benoît Laleu、Mark Lautens

  DOI：10.1021/jo8017236

  日期：2008.11.21

  A variety of six-membered-ring annulated 2H-indazoles and 1,2,3- and 1,2,4-triazoles were synthesized in good to excellent yields from the corresponding bromoethyl azoles and aryl iodides. The annulation process involves a one-pot norbornene-mediated palladium-catalyzed sequence whereby an alkyl-aryl bond and an aryl-heteroaryl bond are successively formed through two C-H bond activations. Subsequent

  从相应的溴乙基唑和芳基碘化物以良好至优异的收率合成了多种六元环环状的2H-吲唑以及1,2,3-和1,2,4-三唑。环合过程涉及一锅降冰片烯介导的钯催化的序列，其中烷基-芳基键和芳基-杂芳基键通过两次CH键激活连续形成。还介绍了通过交叉偶联反应对所得多环化合物的后续官能化作用。
• COMPLEXONES WITH THE STRUCTURE OF N-2-(AZOL-1(2)-YL)ETHYLIMINODIACETIC ACIDS, SYNTHESIS, ANALYTICAL STUDY AND BIOLOGICAL APPLICATIONS
  申请人：UNIVERSIDAD NACIONAL DE EDUCACION A DISTANCIA

  公开号：EP0790241A1

  公开（公告）日：1997-08-20

  Complexones having the structure of N-2-(azol-1(2)-yl(ethyl-iminodiacetic acids, synthesis, analytical study and biological applications, characterized by their complexing capacity over Ca2+, Mg2+ ions and other bivalent cations, lanthanides and transition metals. In the formula azolN-CH2-CH2-N(CH2-CO2R)2 (I), azol is pirazol; 3,5-dimethylpirazol; indazol; etc. and R is alkyl or H or Na. The compounds having the general formula (I), are obtained by an alkylation reaction of methyl iminodiacetate with N-bromoethylazols and further hydrolysis in acid or basic medium. The process may be modified by alternative synthetic processes which involve N-aminoethylazols as starting materials or the use of cyclization processes in the preparation of N-substituted azol. They can be applied in spectroscopy and nuclear magnetic resonance (NMR) imaging of hydrogen or other nuclei as extrinsic probes of Ca2+, Mg2+ or other metal ions and as contrast agents, in solutions, biological extracts, tissues, entire animals and human beings.

  具有 N-2-(azol-1(2)-yl(ethyl-iminodiacetic acids)结构的络合剂的合成、分析研究和生物应用，其特点是对 Ca2+、Mg2+ 离子和其他二价阳离子、镧系元素和过渡金属的络合能力。在式 azolN-CH2-CH2-N(CH2-CO2R)2 (I) 中，azol 是吡唑；3,5-二甲基吡唑；吲唑等，R 是烷基或 H 或 Na。具有通式（I）的化合物是通过亚氨基二乙酸甲酯与 N-溴乙基唑的烷基化反应，并在酸性或碱性介质中进一步水解得到的。该工艺可通过其他合成工艺进行改良，如将 N-氨基乙基偶氮酚作为起始原料，或在制备 N-取代偶氮酚时使用环化工艺。它们可作为 Ca2+、Mg2+ 或其他金属离子的外在探针和造影剂，应用于溶液、生物提取物、组织、整个动物和人体中氢或其他核的光谱学和核磁共振（NMR）成像。
• v. Auwers; Kleiner, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 118, p. 74,90
  作者：v. Auwers、Kleiner

  DOI：——

  日期：——
• N-2-(Azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging
  作者：Pilar López、Christa G Seipelt、Patrick Merkling、Laszlo Sturz、José Álvarez、Andreas Dölle、Manfred D Zeidler、Sebastián Cerdán、Paloma Ballesteros

  DOI：10.1016/s0968-0896(98)00273-9

  日期：1999.3

  The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T-1 and T-2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T-2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. (C) 1999 Elsevier Science Ltd. All rights reserved.