5,5-dimethyl-5,6-dihydropyrazolo[1,5-c]quinazoline | 89399-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,5-dimethyl-5,6-dihydropyrazolo[1,5-c]quinazoline
• 英文别名: 5,6-dihydro-5,5-dimethylpyrazolo[1,5-c]quinazoline；5,5-dimethyl-5,6-dihydro-pyrazolo[1,5-c]quinazoline；2,2-Dimethyl-1,2-dihydro-chinazolin>；5,5-dimethyl-6H-pyrazolo[1,5-c]quinazoline
• CAS: 89399-90-6
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: SLDSXBXAFOMHAA-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  386.2±21.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-硝基苯基)-1H-吡唑 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 8.0h， 生成 5,5-dimethyl-5,6-dihydropyrazolo[1,5-c]quinazoline
  参考文献：
  名称：

  A Simple Synthesis of 5-(2-Aminophenyl)-1H-pyrazoles

  摘要：

  AbstractA four‐step synthesis of 1‐substituted 5‐(2‐aminophenyl)‐1H‐pyrazoles 5 as a novel type of histamine analogs and versatile building blocks for further transformations was developed. The synthesis starts from commercially available 2‐nitroacetophenone (12), which is converted into the enamino ketone 13 as the key intermediate. Cyclization of the key intermediate 13 with monosubstituted hydrazines 14a–14l afforded the 5‐(2‐nitrophenyl)‐1H‐pyrazoles 17a–17l. Finally, catalytic hydrogenation of the nitro compounds 17a, 17c–17e, and 17g–17j furnished the title compounds 5a, 5c–5e, and 5g–5j, respectively, in good yields. As demonstrated by some further transformations, additional functionalization of compounds 17 and 5 is feasible, either by electrophilic substitution at C(4) of the pyrazole ring, or at the NH2 group.

  DOI：

  10.1002/hlca.201100055

文献信息

• Synthesis of 5,6-Dihydropyrazolo[1,5-<i>c</i>]quinazolines through Gold-Catalyzed Chemoselective Bicyclization of <i>N</i>-Propargylic Sulfonylhydrazones
  作者：Hai-Tao Tang、Kai Xiong、Ren-Hao Li、Zong-Cang Ding、Zhuang-Ping Zhan

  DOI：10.1021/ol503437n

  日期：2015.1.16

  of 5,6-dihydropyrazolo[1,5-c]quinazolines via gold(I)-catalyzed chemoselective bicyclization of N-propargylic sulfonylhydrazones has been developed. This process relies on the chemoselective cyclization of the hydrazone nitrogen instead of the usually favored aniline nitrogen onto the alkyne. The synthetic utility of the current strategy is demonstrated through the synthesis of a potential Eg5/Kinesin

  已经开发了一种通过金（I）催化的N-炔丙基磺酰基hydr的化学选择性双环化反应制备5,6-二氢吡唑并[1,5- c ]喹唑啉的有效方法。该方法依赖于nitrogen氮的化学选择性环化，而不是通常偏向苯炔的苯胺氮。通过合成潜在的Eg5 / Kinesin纺锤体蛋白抑制剂，证明了当前策略的合成效用。