ethyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate | 1607814-55-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate
• 英文别名: Ethyl [2-(3-phenylprop-2-ynoyl)phenyl] carbonate；ethyl [2-(3-phenylprop-2-ynoyl)phenyl] carbonate
• CAS: 1607814-55-0
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: FNAWAECMHDZYFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate 在 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以96%的产率得到ethyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
  参考文献：
  名称：

  A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

  摘要：

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.073
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到ethyl 2-(3-phenylprop-2-ynoyl)phenyl carbonate
  参考文献：
  名称：

  A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

  摘要：

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.073

文献信息

• A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization
  作者：Masahito Yoshida、Koya Saito、Yuta Fujino、Takayuki Doi

  DOI：10.1016/j.tet.2014.03.073

  日期：2014.5

  A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c). (C) 2014 Elsevier Ltd. All rights reserved.