2-(2-nitrobenzylamino)propan-1-ol | 223931-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-nitrobenzylamino)propan-1-ol
• 英文别名: 2-{[(2-Nitrophenyl)methyl]amino}propan-1-ol；2-[(2-nitrophenyl)methylamino]propan-1-ol
• CAS: 223931-84-8
• 化学式: C₁₀H₁₄N₂O₃
• mdl: MFCD12184323
• 分子量: 210.233
• InChiKey: VOYYWLSQGMWMKN-UHFFFAOYSA-N

物化性质

• 沸点：
  365.8±22.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-nitrobenzylamino)propan-1-ol 在 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 生成 3-methyl-2,3-dihydrooxazolo[3,2-b]indazole
  参考文献：
  名称：

  Nucleophilic Substitution of Oxazino-/Oxazolino-/Benzoxazin [3,2-b]indazoles: An Effective Route to 1H-Indazolones

  摘要：

  A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.

  DOI：

  10.1021/ol100751n
• 作为产物：
  描述：

  DL-氨基丙醇 、 邻硝基苯甲醛 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(2-nitrobenzylamino)propan-1-ol
  参考文献：
  名称：

  基于两个氢转移反应的金属催化串联 1,4-苯二氮卓合成

  摘要：

  以 2-氨基苄醇和 1,2-氨基醇为原料，2,3,4,5-四氢-1H-1,4-苯二氮卓类（TH-BDZ）可通过一锅钌催化反应制备，包括连续两次借氢循环。首先，苯甲醇氧化，与氨基醇缩合，亚胺还原发生。随后是其他醇官能团的氧化和还原环缩合反应，得到 TH-BDZ 衍生物。一个催化剂完成整个工作，两个水分子是唯一的废物。许多新的取代 2,3,4,5-四氢-1 H -1,4-苯二氮卓类已被制备以证明该方法的多功能性，可用于制备用于药物发现的特权支架。

  DOI：

  10.1002/ejoc.201403261

文献信息

• Nucleophilic Substitution of Oxazino-/Oxazolino-/Benzoxazin [3,2-<i>b</i>]indazoles: An Effective Route to 1<i>H</i>-Indazolones
  作者：Michael B. Donald、Wayne E. Conrad、James S. Oakdale、Jeffrey D. Butler、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/ol100751n

  日期：2010.6.4

  A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.
• Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones
  作者：Aaron Roth、Sean Ott、Kelli M. Farber、Teresa A. Palazzo、Wayne E. Conrad、Makhluf J. Haddadin、Dean J. Tantillo、Carroll E. Cross、Jason P. Eiserich、Mark J. Kurth

  DOI：10.1016/j.bmc.2014.09.044

  日期：2014.11

  Myeloperoxidase (MPO) produces hypohalous acids as a key component of the innate immune response; however, release of these acids extracellularly results in inflammatory cell and tissue damage. The twostep, one-pot Davis-Beirut reaction was used to synthesize a library of 2H-indazoles and 1H-indazolones as putative inhibitors of MPO. A structure-activity relationship study was undertaken wherein compounds were evaluated utilizing taurine-chloramine and MPO-mediated H2O2 consumption assays. Docking studies as well as toxicophore and Lipinski analyses were performed. Fourteen compounds were found to be potent inhibitors with IC50 values < 1 mu M, suggesting these compounds could be considered as potential modulators of pro-oxidative tissue injury pertubated by the inflammatory MPO/H2O2/HOCl/HOBr system. (C) 2014 Elsevier Ltd. All rights reserved.
• A Metal-Catalyzed Tandem 1,4-Benzodiazepine Synthesis Based on Two Hydrogen-Transfer Reactions
  作者：Varsha R. Jumde、Elena Cini、Andrea Porcheddu、Maurizio Taddei

  DOI：10.1002/ejoc.201403261

  日期：2015.2

  (TH-BDZ) can be prepared through a one-pot ruthenium-catalyzed reaction encompassing two consecutive borrowing hydrogen cycles. First, benzyl alcohol oxidation, condensation with the amino alcohol, and imine reduction occurs. This is followed by oxidation of the other alcohol functionality and reductive cyclocondensation to give the TH-BDZ derivatives. A single catalyst does the entire job, with two molecules

  以 2-氨基苄醇和 1,2-氨基醇为原料，2,3,4,5-四氢-1H-1,4-苯二氮卓类（TH-BDZ）可通过一锅钌催化反应制备，包括连续两次借氢循环。首先，苯甲醇氧化，与氨基醇缩合，亚胺还原发生。随后是其他醇官能团的氧化和还原环缩合反应，得到 TH-BDZ 衍生物。一个催化剂完成整个工作，两个水分子是唯一的废物。许多新的取代 2,3,4,5-四氢-1 H -1,4-苯二氮卓类已被制备以证明该方法的多功能性，可用于制备用于药物发现的特权支架。