3-chloro-1H-benzofuro[3,2-c]pyrazole | 1094462-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-chloro-1H-benzofuro[3,2-c]pyrazole
• 英文别名: 3-chloro-2H-[1]benzofuro[3,2-c]pyrazole
• CAS: 1094462-18-6
• 化学式: C₉H₅ClN₂O
• 分子量: 192.605
• InChiKey: PSVBUIHDLMRLMM-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  373.4±22.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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：
  41.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-1H-benzofuro[3,2-c]pyrazole 、 2,6-二甲基苄胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 lithium hexamethyldisilazane 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以62%的产率得到N-(2,6-dimethylphenylmethyl)-1H-benzofuro[3,2-c]pyrazol-3-amine
  参考文献：
  名称：

  An Efficient Intramolecular 1,3-Dipolar Cycloaddition Involving 2-(1,2-Dichlorovinyloxy)aryldiazomethanes: A One-Pot Synthesis of Benzofuropyrazoles from Salicylaldehydes

  摘要：

  A novel intramolecular 1,3-dipolar cycloaddition strategy for a rapid entry into benzofuropyrazoles is described. In it three-step sequence, (E)-2-(1,2-dichlorovinyloxy)aryldiazomethanes were generated in situ from the corresponding salicylaldehydes. Intramolecular cycloaddition followed by dehydrohalogenation garnered 3-chlorobenzofuropyrazoles in excellent yields. By careful choice of solvent, base, and reaction conditions, the entire sequence call be carried Out in a one-pot procedure.

  DOI：

  10.1021/jo802193z
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.17h， 生成 3-chloro-1H-benzofuro[3,2-c]pyrazole
  参考文献：
  名称：

  An Efficient Intramolecular 1,3-Dipolar Cycloaddition Involving 2-(1,2-Dichlorovinyloxy)aryldiazomethanes: A One-Pot Synthesis of Benzofuropyrazoles from Salicylaldehydes

  摘要：

  A novel intramolecular 1,3-dipolar cycloaddition strategy for a rapid entry into benzofuropyrazoles is described. In it three-step sequence, (E)-2-(1,2-dichlorovinyloxy)aryldiazomethanes were generated in situ from the corresponding salicylaldehydes. Intramolecular cycloaddition followed by dehydrohalogenation garnered 3-chlorobenzofuropyrazoles in excellent yields. By careful choice of solvent, base, and reaction conditions, the entire sequence call be carried Out in a one-pot procedure.

  DOI：

  10.1021/jo802193z

文献信息

• An Efficient Intramolecular 1,3-Dipolar Cycloaddition Involving 2-(1,2-Dichlorovinyloxy)aryldiazomethanes: A One-Pot Synthesis of Benzofuropyrazoles from Salicylaldehydes
  作者：Zachary S. Sales、Neelakandha S. Mani

  DOI：10.1021/jo802193z

  日期：2009.1.16

  A novel intramolecular 1,3-dipolar cycloaddition strategy for a rapid entry into benzofuropyrazoles is described. In it three-step sequence, (E)-2-(1,2-dichlorovinyloxy)aryldiazomethanes were generated in situ from the corresponding salicylaldehydes. Intramolecular cycloaddition followed by dehydrohalogenation garnered 3-chlorobenzofuropyrazoles in excellent yields. By careful choice of solvent, base, and reaction conditions, the entire sequence call be carried Out in a one-pot procedure.