ethyl 4-oxo-3-phenyl-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: ethyl 4-oxo-3-phenyl-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate
• 英文别名: ethyl 4-oxo-3-phenyl-3,6-dihydro-1H-furo[3,4-c]pyran-3a-carboxylate
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: OTTBADMURAYMMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  butyne-1,4-diol 、 亚苯甲基丙二酸二乙酯 在 sodium hydride 、 copper(l) iodide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.08h， 以62%的产率得到ethyl 4-oxo-3-phenyl-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates

  摘要：

  A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 31 was the most potent compound with IC50 value of 5.4 mu M. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a, 4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.003

文献信息

• Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates
  作者：Tiantian Wang、Jia Liu、Hanyu Zhong、Huan Chen、Zhiliang Lv、Yikai Zhang、Mingfeng Zhang、Dongping Geng、Chunjuan Niu、Yongmei Li、Ke Li

  DOI：10.1016/j.bmcl.2011.04.003

  日期：2011.6

  A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 31 was the most potent compound with IC50 value of 5.4 mu M. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a, 4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined. (C) 2011 Elsevier Ltd. All rights reserved.