8-(bromomethyl)-2-(2-pyridinyl)quinoline | 136805-55-5

• 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: 8-(bromomethyl)-2-(2-pyridinyl)quinoline
• 英文别名: 8-(bromomethyl)-2-pyridin-2-ylquinoline
• CAS: 136805-55-5
• 化学式: C₁₅H₁₁BrN₂
• 分子量: 299.17
• InChiKey: OYGCRMMLOLBRBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-(bromomethyl)-2-(2-pyridinyl)quinoline 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.5h， 生成 trans-8-<2-(7-methyl-2-naphthalenyl)ethenyl>-2-(2-pyridinyl)quinoline
  参考文献：
  名称：

  Synthesis of the helicopodands: novel shapes for chiral clefts

  摘要：

  Helicopodands are a new class of chiral nonmacrocyclic ("podand") receptors with a helicene backbone ("helico"). At the termini of the helix, they form a preorganized cleft of pronounced asymmetric character which is aligned with convergent hydrogen bonding functionality. The synthetic routes to the two helicopodands 2 and 3 each include two photocyclodehydrogenation reactions. The X-ray crystal structure of 14, a direct helical precursor to 2 and 3, confirms the main structural features of the helicopodands. MMP2 calculations give a geometric description of 14 which is in reasonable agreement with the X-ray results.

  DOI：

  10.1021/jo00024a017
• 作为产物：
  描述：

  砒啶-2-硼酸二甲酯 在 四(三苯基膦)钯 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 四乙基溴化铵 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 9.25h， 生成 8-(bromomethyl)-2-(2-pyridinyl)quinoline
  参考文献：
  名称：

  Synthesis of the helicopodands: novel shapes for chiral clefts

  摘要：

  Helicopodands are a new class of chiral nonmacrocyclic ("podand") receptors with a helicene backbone ("helico"). At the termini of the helix, they form a preorganized cleft of pronounced asymmetric character which is aligned with convergent hydrogen bonding functionality. The synthetic routes to the two helicopodands 2 and 3 each include two photocyclodehydrogenation reactions. The X-ray crystal structure of 14, a direct helical precursor to 2 and 3, confirms the main structural features of the helicopodands. MMP2 calculations give a geometric description of 14 which is in reasonable agreement with the X-ray results.

  DOI：

  10.1021/jo00024a017

文献信息

• Synthesis of the helicopodands: novel shapes for chiral clefts
  作者：Kurt Deshayes、Richard D. Broene、Ito Chao、Carolyn B. Knobler、Francois Diederich

  DOI：10.1021/jo00024a017

  日期：1991.11

  Helicopodands are a new class of chiral nonmacrocyclic ("podand") receptors with a helicene backbone ("helico"). At the termini of the helix, they form a preorganized cleft of pronounced asymmetric character which is aligned with convergent hydrogen bonding functionality. The synthetic routes to the two helicopodands 2 and 3 each include two photocyclodehydrogenation reactions. The X-ray crystal structure of 14, a direct helical precursor to 2 and 3, confirms the main structural features of the helicopodands. MMP2 calculations give a geometric description of 14 which is in reasonable agreement with the X-ray results.