2-benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3(2H)-one | 929190-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3(2H)-one
• 英文别名: 2-Benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3-one；2-benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3-one
• CAS: 929190-86-3
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: LVKMRKMBKRGCLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3(2H)-one 在 盐酸 、 二氮烯 、 sodium nitrite 作用下， 反应 4.0h， 生成 5-azido-2-benzyl-4-(4-chlorophenyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles

  摘要：

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.

  DOI：

  10.3987/com-06-10879
• 作为产物：
  描述：

  4-氯苯硼酸 、 2-苄基-4-氯-5-甲氧基-3(2H-)-吡嗪酮 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以95%的产率得到2-benzyl-4-(4-chlorophenyl)-5-methoxypyridazin-3(2H)-one
  参考文献：
  名称：

  Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles

  摘要：

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.

  DOI：

  10.3987/com-06-10879

文献信息

• Synthesis of (Hetero)arylated Pyridazin-3(2<i>H</i>)-ones via Negishi Reaction Involving Zincated Pyridazin-3(2<i>H</i>)-ones
  作者：Tom Verhelst、Zuming Liu、Jens Maes、Bert U. W. Maes

  DOI：10.1021/jo201587j

  日期：2011.12.2

  Zincated pyridazin-3(2H)-ones generated via bromine–magnesium exchange followed by transmetalation using ZnCl2 or via lactam-directed ortho C4-H zincation with TMPZnCl·LiCl have been synthesized. These in situ created organometallics can be used in Negishi reactions with iodo(hetero)arenes delivering a new approach toward (hetero)arylpyridazin-3(2H)-ones.

  合成了通过溴-镁交换，然后使用ZnCl 2进行金属转移或通过内酰胺定向的邻位C4-H锌与TMPZnCl·LiCl生成的锌哒嗪3（2 H）- 。这些原位生成的有机金属化合物可用于Negishi与碘（杂）芳烃的反应，从而为（杂）芳基哒嗪3（2 H）-酮提供了一种新方法。
• Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles
  作者：Norbert Haider、Andrea Wobus

  DOI：10.3987/com-06-10879

  日期：——

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.