dimethyl 5-benzyl-4-phenylfuran-2,3-dicarboxylate | 1369592-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: dimethyl 5-benzyl-4-phenylfuran-2,3-dicarboxylate
• 英文别名: Dimethyl 5-benzyl-4-phenylfuran-2,3-dicarboxylate
• CAS: 1369592-87-9
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: OUZQXIOAGVLUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,4-二苯基-3-丁炔-2-醇 在 三乙烯二胺 、 四丁基氟化铵 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 dimethyl 5-benzyl-4-phenylfuran-2,3-dicarboxylate
  参考文献：
  名称：

  Palladium-catalyzed one-pot synthesis of polysubstituted furans from alkynoates and 2-yn-1-ols

  摘要：

  Easily accessible propargyl vinyl ethers are found to be acyclic precursors to construct furan derivatives. According to the reactive behavior of the substrates and the regulation of reaction conditions, three synthetic routes to polysubstituted furans via palladium-catalyzed reactions of propargyl vinyl ethers in situ-prepared from alkynoates and 2-yn-1-ols are presented herein. These methods could have potential application in synthetic and pharmaceutical chemistry for its facilitation and accessible starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.033

文献信息

• An Efficient and General Iron-Catalyzed One-Pot Synthesis of Furans via α-Hydroxy Ketones and Activated Alkynes
  作者：Hua Cao、Haiying Zhan、Jianyong Wu、Haiping Zhong、Yuanguang Lin、Hong Zhang

  DOI：10.1002/ejoc.201200163

  日期：2012.4

  A new practical and economical process for the synthesis of substituted furan derivatives has been developed by an FeCl3-catalyzed reaction of α-hydroxy ketones with activated alkynes. This methodology represents a highly efficient synthetic route to electron-deficient furans for which catalytic approaches are scarce. Furthermore, this transformation is associated with readily available substrates

  通过 FeCl3 催化 α-羟基酮与活化炔烃的反应，开发了一种新的实用且经济的合成取代呋喃衍生物的方法。这种方法代表了一种高效的缺电子呋喃合成路线，催化方法稀缺。此外，这种转化与容易获得的底物、良好的产量和温和的条件有关。
• DABCO-Catalyzed Synthesis of Trifluoromethylated Furans from Propargyl Alcohols and Methyl 2-Perfluoroalkynoate
  作者：Qinglei Chong、Xiaoyi Xin、Chunxiang Wang、Fan Wu、Haolong Wang、Ji-cheng Shi、Boshun Wan

  DOI：10.1021/jo4028424

  日期：2014.3.7

  The DABCO-catalyzed reaction of propargyl alcohols with methyl 2-perfluoroalkynoate to give trifluoromethylated furans in up to 98% yield under mild conditions has been developed. The established allene-enol and control experiments indicate that the reaction should proceed through a Michael addition and Claisen rearrangement/cyclization process.
• Palladium-catalyzed one-pot synthesis of polysubstituted furans from alkynoates and 2-yn-1-ols
  作者：Huawen Huang、Huanfeng Jiang、Hua Cao、Jinwu Zhao、Dabin Shi

  DOI：10.1016/j.tet.2011.12.033

  日期：2012.4

  Easily accessible propargyl vinyl ethers are found to be acyclic precursors to construct furan derivatives. According to the reactive behavior of the substrates and the regulation of reaction conditions, three synthetic routes to polysubstituted furans via palladium-catalyzed reactions of propargyl vinyl ethers in situ-prepared from alkynoates and 2-yn-1-ols are presented herein. These methods could have potential application in synthetic and pharmaceutical chemistry for its facilitation and accessible starting materials. (C) 2011 Elsevier Ltd. All rights reserved.