2-nitro-1-<4-(trifluoromethyl)phenyl>-1-propanol | 21886-16-8

• 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-nitro-1-<4-(trifluoromethyl)phenyl>-1-propanol
• 英文别名: 2-nitro-1-(4-(trifluoromethyl) phenyl) propan-1-ol；2-nitro-1-[4-(trifluoromethyl)phenyl]propan-1-ol
• CAS: 21886-16-8
• 化学式: C₁₀H₁₀F₃NO₃
• 分子量: 249.19
• InChiKey: ATUMVGCOAUQVPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitro-1-<4-(trifluoromethyl)phenyl>-1-propanol 在 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-methyl-1-nitro-2-<4-(trifluoromethyl)phenyl>ethene
  参考文献：
  名称：

  Inter- and intramolecular [4 + 2] cycloadditions of nitroalkenes with olefins. 2-Nitrostyrenes

  摘要：

  Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.

  DOI：

  10.1021/jo00044a029
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 硝基乙烷 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 2-nitro-1-<4-(trifluoromethyl)phenyl>-1-propanol
  参考文献：
  名称：

  Case Study of Small Molecules As Antimalarials: 2-Amino-1-phenylethanol (APE) Derivatives

  摘要：

  Antiparasitic oral drugs have been associated to lipophilic molecules due to their intrinsic permeability. However, these kind of molecules are associated to numerous adverse effects, which have been extensively studied. Within the Tres Cantos Antimalarial Set (TCAMS) we have identified two small, soluble and simple hits that even presenting antiplasmodial activities in the range of 0.4-0.5 mu M are able to show in vivo activity.

  DOI：

  10.1021/ml500015r

文献信息

• <i>anti</i>-Selective Asymmetric Henry Reaction Catalyzed by a Heterobimetallic Cu–Sm–Aminophenol Sulfonamide Complex
  作者：Yang Li、Ping Deng、Youmao Zeng、Yan Xiong、Hui Zhou

  DOI：10.1021/acs.orglett.6b00432

  日期：2016.4.1

  A novel heterobimetallic Cu/Sm/aminophenol sulfonamide complex has been developed by a convenient one-pot method for the anti-selective asymmetric Henry reaction. The corresponding anti-β-nitro alcohols are obtained in up to 99% yield, >30:1 dr, and 98% ee. The results of control experiments and ESI-MS analysis of the complex indicate that the monomeric bimetallic Cu/Sm/1 complex would be the active

  通过方便的一锅法开发了一种新型的双金属Cu / Sm /氨基苯酚磺酰胺络合物，用于抗选择性不对称亨利反应。以高达99％的收率，＞ 30∶1的dr和98％的ee获得相应的抗-β-硝基醇。配合物的对照实验和ESI-MS分析结果表明，单体双金属Cu / Sm / 1配合物是活性物质。
• Inter- and intramolecular [4 + 2] cycloadditions of nitroalkenes with olefins. 2-Nitrostyrenes
  作者：Scott E. Denmark、Brenda S. Kesler、Young Choon Moon

  DOI：10.1021/jo00044a029

  日期：1992.8

  Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.
• Case Study of Small Molecules As Antimalarials: 2-Amino-1-phenylethanol (APE) Derivatives
  作者：María J. Chaparro、Jaume Vidal、Íñigo Angulo-Barturen、José M. Bueno、Jeremy Burrows、Nicholas Cammack、Pablo Castañeda、Gonzalo Colmenarejo、José M. Coterón、Laura de las Heras、Esther Fernández、Santiago Ferrer、Raquel Gabarró、Francisco J. Gamo、Mercedes García、María B. Jiménez-Díaz、María J. Lafuente、María L. León、María S. Martínez、Douglas Minick、Sara Prats、Margarita Puente、Lourdes Rueda、Elena Sandoval、Ángel Santos-Villarejo、Michael Witty、Félix Calderón

  DOI：10.1021/ml500015r

  日期：2014.6.12

  Antiparasitic oral drugs have been associated to lipophilic molecules due to their intrinsic permeability. However, these kind of molecules are associated to numerous adverse effects, which have been extensively studied. Within the Tres Cantos Antimalarial Set (TCAMS) we have identified two small, soluble and simple hits that even presenting antiplasmodial activities in the range of 0.4-0.5 mu M are able to show in vivo activity.