(Z)-5-benzylidene-4-hydroxy-3-(2-methoxyphenyl)furan-2(5H)-one | 1291089-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-benzylidene-4-hydroxy-3-(2-methoxyphenyl)furan-2(5H)-one
• 英文别名: (5Z)-5-benzylidene-4-hydroxy-3-(2-methoxyphenyl)furan-2-one
• CAS: 1291089-07-0
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: RLCCMUQOSBAVRY-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  syn-methyl 2-hydroxy-3-phenyl-3-(2,2,2-trifluoroethoxy)propanoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.25h， 生成 (Z)-5-benzylidene-4-hydroxy-3-(2-methoxyphenyl)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis of pulvinones via tandem Dieckmann condensation–alkoxide β-elimination

  摘要：

  A series of pulvinones were prepared in three steps from a common precursor, methyl 3-phenylglycidate. This compound was readily converted to several diesters containing an ether function. Then, treatment of these compounds with lithium hexamethyldisilazide afforded the corresponding pulvinones, via tandem Dieckmann condensation-alkoxide beta-elimination. The use of a 2,2,2-trifluoroethyl ether instead of a methyl ether facilitated the beta-elimination and led to better yields of product. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.011

文献信息

• Synthesis of pulvinones via tandem Dieckmann condensation–alkoxide β-elimination
  作者：Brice Nadal、Julien Rouleau、Hélène Besnard、Pierre Thuéry、Thierry Le Gall

  DOI：10.1016/j.tet.2011.02.011

  日期：2011.4

  A series of pulvinones were prepared in three steps from a common precursor, methyl 3-phenylglycidate. This compound was readily converted to several diesters containing an ether function. Then, treatment of these compounds with lithium hexamethyldisilazide afforded the corresponding pulvinones, via tandem Dieckmann condensation-alkoxide beta-elimination. The use of a 2,2,2-trifluoroethyl ether instead of a methyl ether facilitated the beta-elimination and led to better yields of product. (C) 2011 Elsevier Ltd. All rights reserved.