(R)-1-(3-phenoxyphenyl)-but-3-enyl acrylate | 1115246-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(3-phenoxyphenyl)-but-3-enyl acrylate
• 英文别名: [(1R)-1-(3-phenoxyphenyl)but-3-enyl] prop-2-enoate
• CAS: 1115246-92-8
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: XSOIIXHHZMPTGN-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-phenoxyphenyl)-but-3-en-1-ol 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-1-(3-phenoxyphenyl)-but-3-enyl acrylate 、 (R)-1-(3-phenoxyphenyl)-but-3-enyl acrylate
  参考文献：
  名称：

  6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

  摘要：

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.069