o,p-dimethoxycinnamyl alcohol | 1363130-07-7

• 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: o,p-dimethoxycinnamyl alcohol
• 英文别名: 3-(2,4-Dimethoxyphenyl)prop-2-en-1-ol；(E)-3-(2,4-dimethoxyphenyl)prop-2-en-1-ol
• CAS: 1363130-07-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: LDHOYRRZKJKQBY-ONEGZZNKSA-N

物化性质

• 沸点：
  355.3±32.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o,p-dimethoxycinnamyl alcohol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 生成 (E)-3-(2,4-dimethoxyphenyl)acrylaldehyde
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059
• 作为产物：
  描述：

  （E）-3-（2,4-二甲氧基苯基）丙烯酸乙酯 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以94%的产率得到o,p-dimethoxycinnamyl alcohol
  参考文献：
  名称：

  Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions

  摘要：

  Structurally novel endoperoxides can be sythesized by the photocatalytic cyclotrimerization of bis(styrene) substrates with molecular oxygen. The optimal catalyst for this process is Ru(bpz)(3)(2+), which is a markedly more efficient catalyst for these photooxygention reactions than conventional organic photosensitizers. The 1,2-dioxolane products are amenable to synthetic manipulation and can be easily processed to 1,4-diols and gamma-hydroxyketones. An initial screen of the biological activity of these compounds reveals promising inhibition of cancer cell growth.

  DOI：

  10.1021/ol300428q