N-(3,4-dimethoxyphenyl)-4-trifluoromethylbenzylidenimine | 1169830-49-2

• 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: N-(3,4-dimethoxyphenyl)-4-trifluoromethylbenzylidenimine
• CAS: 1169830-49-2
• 化学式: C₁₆H₁₄F₃NO₂
• 分子量: 309.288
• InChiKey: HZDUUIGHQZMGFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-环己烯-1-酮 、 N-(3,4-dimethoxyphenyl)-4-trifluoromethylbenzylidenimine 在 (S)-N-(4-十二烷基苯磺酰基)吡咯烷-2-甲酰胺 作用下， 反应 96.0h， 以49%的产率得到(1S,3S,4S)-2-(3,4-dimethoxyphenyl)-3-(4-trifluoromethylphenyl)-2-aza-bicyclo[2.2.2]octan-5-one
  参考文献：
  名称：

  Asymmetric Construction of Nitrogen-Containing [2.2.2] Bicyclic Scaffolds Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide

  摘要：

  An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.

  DOI：

  10.1021/jo9009062
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 3,4-二甲氧基苯胺 以 苯 为溶剂， 反应 5.0h， 以89%的产率得到N-(3,4-dimethoxyphenyl)-4-trifluoromethylbenzylidenimine
  参考文献：
  名称：

  Asymmetric Construction of Nitrogen-Containing [2.2.2] Bicyclic Scaffolds Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide

  摘要：

  An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.

  DOI：

  10.1021/jo9009062

文献信息

• Asymmetric Synthesis of Indolines through Intramolecular Shifting of Aromatic Sulfinyl Groups. Role of the π,π-Stacking Interactions in these Unusual S_NAr Processes
  作者：José L. García Ruano、Alejandro Parra、Vanesa Marcos、Carlos del Pozo、Silvia Catalán、Silvia Monteagudo、Santos Fustero、Ana Poveda

  DOI：10.1021/ja8096527

  日期：2009.7.8

  Cyclization of N-aryl substituted 1-aryl-2[2-p-tolylsulfinyl]phenyl propylamines under LDA, LHMDS, or KHMDS provides a new approach for synthesizing optically pure 2,3-disubstituted indolines. Both the scope and the limitations of this method have been investigated. The pi,pi-stacking interactions are crucial for these unprecedented intramolecular S(N)Ar processes, in which a sulfinyl group located

  N-芳基取代的 1-芳基-2[2-p-tolylsulfinyl] 苯基丙胺在 LDA、LHMDS 或 KHMDS 下的环化为合成光学纯 2,3-二取代二氢吲哚提供了一种新方法。已经研究了该方法的范围和局限性。pi,pi 堆积相互作用对于这些前所未有的分子内 S(N)Ar 过程至关重要，其中位于轻微失活环上的亚磺酰基在温和条件下被酰胺阴离子取代。提供了支持这些 pi,pi-stacking 相互作用的 X 射线和 NMR 证明。
• Development of Novel Vitamin D Receptor–Coactivator Inhibitors
  作者：Preetpal S. Sidhu、Nicholas Nassif、Megan M. McCallum、Kelly Teske、Belaynesh Feleke、Nina Y. Yuan、Premchendar Nandhikonda、James M. Cook、Rakesh K. Singh、Daniel D. Bikle、Leggy A. Arnold

  DOI：10.1021/ml400462j

  日期：2014.2.13

  Nuclear receptor coregulators are master regulators of transcription and selectively interact with the vitamin D receptor (VDR) to modulate cell differentiation, cell proliferation, and calcium homeostasis. Herein, we report the syntheses and evaluation of highly potent and selective VDR-coactivator inhibitors based on a recently identified 3-indolylmethanamine scaffold. The most active compound, PS121912, selectively inhibited VDR-mediated transcription among eight other nuclear receptors tested. PS121912 is also selectively disrupting the binding between VDR and the third nuclear receptor interaction domain of the coactivator SRC2. Genetic studies revealed that PS121912 behaves. like a VDR antagonist by repressing 1,25-(OH)(2)D-3 activated gene transcription. In addition, PS121912 induced apoptosis in HL-60.