吖啶(D9) | 34749-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 吖啶(D9)
• 英文名称: acridine-d9
• 英文别名: Acridin-d(9)；Acridine (D9)；1,2,3,4,5,6,7,8,9-nonadeuterioacridine
• CAS: 34749-75-2
• 化学式: C₁₃H₉N
• 分子量: 188.15
• InChiKey: DZBUGLKDJFMEHC-LOIXRAQWSA-N

物化性质

• 溶解度：
  DMSO（轻微，超声处理），甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吖啶 在 palladium(II) trifluoroacetate 、 重水 、 2,4,6-triisopropyl-N-(quinolin-8-yl)benzamide 作用下， 以95 %的产率得到吖啶(D9)
  参考文献：
  名称：

  Palladium(II)‐Catalyzed Nondirected Late‐Stage C(sp2)−H Deuteration of Heteroarenes Enabled Through a Multi‐Substrate Screening Approach

  摘要：

  The importance of deuterium labelling in a variety of applications, ranging from mechanistic studies to drug‐discovery, has spurred immense interest in the development of new methods for its efficient incorporation in organic, and especially in bioactive molecules. The five‐membered heteroarenes at the center of this work are ubiquitous motifs in bioactive molecules and efficient methods for the deuterium labelling of these compounds are therefore highly desirable. However, the profound differences in chemical properties encountered between different heteroarenes hamper the development of a single set of broadly applicable reaction conditions, often necessitating a separate optimization campaign for a given type of heteroarene. In this study we describe the use of a multi‐substrate screening approach to identify optimal reaction conditions for different classes of heteroarenes from a minimal number of screening reactions. Using this approach, four sets of complementary reaction conditions derived from our dual ligand‐based palladium catalysts for nondirected C(sp2)–H activation were identified, that together enable the deuteration of structurally diverse heteroarenes, including bioactive molecules.

  DOI：

  10.1002/anie.202404421