1-(3'-Pyridyl)-2-nitro-propen-1 | 3156-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3'-Pyridyl)-2-nitro-propen-1
• 英文别名: 3-(2-Nitro-1-propen-1-yl)pyridine；3-(2-nitroprop-1-enyl)pyridine
• CAS: 3156-53-4
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: RUSUNWVZTBJUHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3'-Pyridyl)-2-nitro-propen-1 在 盐酸 、 三氯化铁 、 铁粉 作用下， 以 水 为溶剂， 生成 3-(2-氧代丙基)-氯化吡啶
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  3-吡啶甲醛 、 硝基乙烷 在 ammonium acetate 作用下， 生成 1-(3'-Pyridyl)-2-nitro-propen-1
  参考文献：
  名称：

  通过酶促光氧化还原催化硝基烷烃的不对称 C-烷基化

  摘要：

  叔硝基烷烃和相应的α-叔胺代表了生物活性分子和天然产物中的重要基序。仲硝基烷烃与亲电子试剂的C烷基化是构建叔硝基烷烃的简单策略；然而，控制此类反应的立体选择性仍然具有挑战性。在这里，我们报道了由工程黄素依赖性“烯”还原酶（ERED）催化的硝基烷烃与卤代烷的高度化学和立体选择性C烷基化。来自嗜土芽孢杆菌的老黄色酶的定向进化提供了三重突变体 GkOYE-G7，能够以高产率和对映选择性合成叔硝基烷烃。机理研究表明，底物和辅因子之间形成的酶模板电荷转移复合物的激发是自由基引发的原因。此外，还开发了一种单酶双机制级联反应，可以从简单的硝基烯烃制备叔硝基烷烃，突出了使用一种酶进行两种机制不同的反应的潜力。

  DOI：

  10.1021/jacs.2c12197

文献信息

• [EN] 3-SUBSTITUTED 1,2,3-TRIAZIN-4-ONE'S AND 3-SUBSTITUTED 1,3-PYRIMIDINONE'S FOR ENHANCING GLUTAMATERGIC SYNAPTIC RESPONSES<br/>[FR] 1,2,3-TRIAZINE-4-ONES 3-SUBSTITUÉES ET 1,3-PYRIMIDINONES 3-SUBSTITUÉES POUR AMÉLIORER LES RÉPONSES SYNAPTIQUES GLUTAMATERGIQUES
  申请人：CORTEX PHARMA INC

  公开号：WO2009038752A3

  公开（公告）日：2009-07-09
• Palladium-Catalyzed Asymmetric Decarboxylative [4+2] Dipolar Cycloaddition of 4-Vinyl-1,3-dioxan-2-ones with α,β-Disubstituted Nitroalkenes Enabled by a Benzylic Substituted P,N-Ligand
  作者：Juan Du、Yuan-Da Hua、Yang-Jie Jiang、Shuai Huang、Di Chen、Chang-Hua Ding、Xue-Long Hou

  DOI：10.1021/acs.orglett.0c01638

  日期：2020.7.17

  The Pd-catalyzed asymmetric [4+2] cycloaddition reaction of an aliphatic 1,4-dipole with singly activated electron-deficient alkenes is realized for the first time, enabled by using a newly developed benzylic substituted P,N-ligand, affording tetrahydropyrans having three continuous chiral centers in high yields with high diastereo- and enantioselectivities. The rational transition states of the reaction as well as the role of the benzylic chiral center are proposed.
• Some Pyridylnitroalkenes, Nitroalkanols, and Alkylamines
  作者：ALFRED BURGER、M. LUISA STEIN、JOHN B. CLEMENTS

  DOI：10.1021/jo01353a010

  日期：1957.2
• The [1 + 4] cycloaddition of isocyanides with 1-aryl-2-nitro-1-propenes. Methyl 2-nitro-3-arylpropenoates and methyl 2-nitro-2,4-pentadienoates. Synthesis of 1-hydroxyindoles and 1-hydroxypyrroles
  作者：Andre Foucaud、Claudia Razorilalana-Rabearivony、Emile Loukakou、Herve Person

  DOI：10.1021/jo00169a004

  日期：1983.10
• Magdesieva, N. N.; Sergeeva, T. A.; Kyandzhetsian, R. A., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 9, p. 1813 - 1815
  作者：Magdesieva, N. N.、Sergeeva, T. A.、Kyandzhetsian, R. A.

  DOI：——

  日期：——