6-(prop-2-yn-1-yloxy)benzofuran-3(2H)-one | 1339888-63-9

• 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: 6-(prop-2-yn-1-yloxy)benzofuran-3(2H)-one
• 英文别名: 6-Prop-2-ynoxy-1-benzofuran-3-one
• CAS: 1339888-63-9
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: QKRKQSCYKZOMGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  6-(prop-2-yn-1-yloxy)benzofuran-3(2H)-one 、 N-(benzyloxy)-2-bromo-2-methylpropanamide 在 N,N-diisopropanolamine 作用下， 反应 12.0h， 以95%的产率得到3′-(benzyloxy)-5′,5′-dimethyl-6-(prop-2-yn-1-yloxy)-2H-spiro[benzofuran-3,2′-oxazolidin]-4′-one
  参考文献：
  名称：

  [3 + 2]带有环酮的环氧基氮杂烯丙基阳离子的加成反应：获得Spiro-4-恶唑烷酮类化合物

  摘要：

  使用温和的反应条件，已经开发出了第一个正式的[3 + 2]环加成反应，该反应是原位生成的氮杂烯丙基阳离子与环酮的反应。以优异的产率（高达99％）获得了各种螺-4-恶唑烷酮。该方法的高效率以及操作简便性使其成为合成螺4-恶唑烷酮的有吸引力的方法。

  DOI：

  10.1021/acs.joc.7b01728

文献信息

• A mild protocol for efficient preparation of functional molecules containing triazole
  作者：Jing Leng、Jie Xu、Yanan Li、Shi-Meng Wang、Hua-Li Qin

  DOI：10.1039/d4ra01271b

  日期：——

  The construction of a class of novel triazole molecules containing sulfonyl fluoride functionalities was achieved through Cu-catalyzed click chemistry in good to excellent yields. The sulfonyl fluoride moieties were cleaved completely under base conditions to produce N-unsubstituted triazoles quantitatively, which provides a strategy to combine SuFEx click chemistry with Cu-catalyzed click chemistry

  通过铜催化的点击化学，以良好至优异的收率构建了一类含有磺酰氟官能团的新型三唑分子。磺酰氟部分在碱性条件下完全裂解，定量产生N-未取代的三唑，这提供了将SuFEx点击化学与Cu催化点击化学巧妙结合的策略。
• From a Natural Product Lead to the Identification of Potent and Selective Benzofuran-3-yl-(indol-3-yl)maleimides as Glycogen Synthase Kinase 3β Inhibitors That Suppress Proliferation and Survival of Pancreatic Cancer Cells
  作者：Irina N. Gaisina、Franck Gallier、Andrei V. Ougolkov、Ki H. Kim、Toru Kurome、Songpo Guo、Denise Holzle、Doris N. Luchini、Sylvie Y. Blond、Daniel D. Billadeau、Alan P. Kozikowski

  DOI：10.1021/jm801317h

  日期：2009.4.9

  Recent studies have demonstrated that glycogen synthase kinase 3 beta (GSK-3 beta) is overexpressed in human colon and pancreatic carcinomas, contributing to cancer cell proliferation and survival. Here, we report the design, synthesis, and biological evaluation of benzofuran-3-yl-(indol-3-yl)maleimides, potent GSK-3 beta inhibitors. Some of these compounds show picomolar inhibitory activity toward GSK-3 beta and an enhanced selectivity against cycl in-dependent kinase 2 (CDK-2). Selected GSK-3 beta inhibitors were tested in the pancreatic cancer cell lines MiaPaCa-2, BXPC-3, and HupT3. We determined that some of these compounds, namely compounds 5, 6, 11, 20, and 26, demonstrate antiproliferative activity against some or all of the pancreatic cancer cells at low micromolar to nanomolar concentrations. We found that the treatment of pancreatic cancer cells with GSK-3 beta inhibitors 5 and 26 resulted in suppression of GSK-3 beta activity and a distinct decrease of the X-linked inhibitor of apoptosis (XIAP) expression, leading to significant apoptosis. The present data suggest a possible role for GSK-3 beta inhibitors in cancer therapy, in addition to their more prominent applications in CNS disorders.
• [3 + 2] Cycloaddition of Azaoxyallyl Cations with Cyclic Ketones: Access to Spiro-4-oxazolidinones
  作者：Pan-Lin Shao、Zi-Rui Li、Zhi-Peng Wang、Ming-Hui Zhou、Qi Wu、Ping Hu、Yun He

  DOI：10.1021/acs.joc.7b01728

  日期：2017.10.6

  The first formal [3 + 2] cycloaddition reaction of in situ generated azaoxyallyl cation with cyclic ketones has been developed using mild reaction conditions. A variety of spiro-4-oxazolidinones was obtained in excellent yields (up to 99%). The high efficiency of this process, coupled with the operational simplicity, makes it an attractive method for the synthesis of spiro-4-oxazolidinones.

  使用温和的反应条件，已经开发出了第一个正式的[3 + 2]环加成反应，该反应是原位生成的氮杂烯丙基阳离子与环酮的反应。以优异的产率（高达99％）获得了各种螺-4-恶唑烷酮。该方法的高效率以及操作简便性使其成为合成螺4-恶唑烷酮的有吸引力的方法。