(1,4-dihydroxy-2-naphthyl)-2-buten-1-one | 140660-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1,4-dihydroxy-2-naphthyl)-2-buten-1-one
• 英文别名: 1,4-dihydroxy-2-crotonoylnaphthalene；1-(1,4-dihydroxynaphthalen-2-yl)but-2-en-1-one
• CAS: 140660-45-3
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: XHOLFISCHAITBY-UHFFFAOYSA-N

物化性质

• 沸点：
  479.8±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,4-萘醌 、 丁烯-2-醛 以 苯 为溶剂， 反应 144.0h， 以72%的产率得到(1,4-dihydroxy-2-naphthyl)-2-buten-1-one
  参考文献：
  名称：

  The cytotoxic effect of 2-acylated-1,4-naphthohydroquinones on leukemia/lymphoma cells

  摘要：

  Here, we tested seven 2-acylated-1,4-hydronaphthoquinones for their cytotoxic effects on a panel of cancer lymphoma/leukemia cells and compared to a non-cancer origin cell line. Several naphthohydroquinones exhibited selective cytotoxic effects on lymphoma/leukemia cells with lowest activity on non-cancer cells. The mode of cell death induced by an acylated naphthohydroquinone, which has a long alkyl chain, was found to be via apoptosis. Furthermore, the naphthohydroquinone provoked mitochondria depolarization and activation of its downstream effector, caspase-3, thus implicating the intrinsic apoptotic pathway as its mechanism to exert cell death. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.007

文献信息

• Green photochemistry: photo-Friedel–Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids
  作者：Brian Murphy、Peter Goodrich、Christopher Hardacre、Michael Oelgemöller

  DOI：10.1039/b913252j

  日期：——

  The photo-Friedel–Crafts acylation of 1,4-naphthoquinone with various aldehydes was investigated in a series of room temperature ionic liquids. High conversions and selectivities were achieved in [C2mim]+-based ionic liquids with the highest isolated yields found in [C2mim][NTf2]. The developed procedure allowed for a replacement of hazardous solvents such as benzene and acetonitrile which are commonly used for this transformation.

  在一系列室温离子液体中研究了 1,4-萘醌与各种醛的光-弗里德尔-卡夫酰化反应。在[C2mim]+基离子液体中实现了高转化率和高选择性，其中[C2mim][NTf2]的分离产率最高。所开发的程序可以替代苯和乙腈等危险溶剂，这些溶剂通常用于这种转化。
• Quinone photochemistry. A general synthesis of acylhydroquinones
  作者：George A. Kraus、Masayuki Kirihara

  DOI：10.1021/jo00037a058

  日期：1992.5