7-(prop-2-yn-1-yloxy)-4H-chromen-4-one | 1348630-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-(prop-2-yn-1-yloxy)-4H-chromen-4-one
• 英文别名: 7-(prop-2-ynyloxy)-4H-benzopyran-4-one；7-(2-Propynyloxy)chromone；7-prop-2-ynoxychromen-4-one
• CAS: 1348630-12-5
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: YTIFOJMYHBDZSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(prop-2-yn-1-yloxy)-4H-chromen-4-one 、 2-溴溴苄 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以76%的产率得到7-((1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry

  摘要：

  Based on the advantages of natural products in new anti-cancer drug development, we synthesized a series of novel benzopyran-4-one derivatives and evaluated their in vitro anti-cancer activities. The bioassays showed that the majority of the resultant compounds exerted anti-tumor effect against six human cancer cell lines to various extents, which supported the rationale of the design. Compound 5s exhibited highest potency of all the synthesized compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.026
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 高氯酸 、 水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.0h， 生成 7-(prop-2-yn-1-yloxy)-4H-chromen-4-one
  参考文献：
  名称：

  Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry

  摘要：

  Based on the advantages of natural products in new anti-cancer drug development, we synthesized a series of novel benzopyran-4-one derivatives and evaluated their in vitro anti-cancer activities. The bioassays showed that the majority of the resultant compounds exerted anti-tumor effect against six human cancer cell lines to various extents, which supported the rationale of the design. Compound 5s exhibited highest potency of all the synthesized compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.026

文献信息

• I2/DTBP promoted synthesis of C3-carbonylated imidazopyridines from chromones and 2-aminopyridines via (3+2) cycloaddition
  作者：Qiang Huang、Lvjia Wu、Jihai Shi、Jiangdong Li、Wei Lu、Fushan Tang、Lei Zhu、Wenwu Zhong、Changkuo Zhao

  DOI：10.1055/a-2058-0119

  日期：——

  An I2/DTBP-promoted (3+2) cycloaddition reaction of 2-aminopyridines and chromones is reported. The work provides a simple and efficient approach to access imidazopyridines scaffold in moderate to good yields. I2/DTBP as an initiator and oxidant was used to realize the tandem (3+2) cycloaddition/oxidative aromatization. Available starting materials, excellent functional-group tolerance, potential drug

  报道了I 2 /DTBP 促进的 2-氨基吡啶和色酮的 (3+2) 环加成反应。这项工作提供了一种简单有效的方法来获得中等至良好产量的咪唑并吡啶支架。I 2 /DTBP作为引发剂和氧化剂用于实现串联（3+2）环加成/氧化芳构化。可用的起始材料、优异的官能团耐受性、产品的潜在药物活性以及在克级生产中的应用是该策略的优势特征。此外，所得产物为卡博替尼类似物的合成提供了关键活性片段，具有开发为抗癌药物的潜力。