4-hydroxy-2-methoxycinnamaldehyde | 127321-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-2-methoxycinnamaldehyde
• 英文别名: 4-hydroxy-2-methoxycinnamal；2-Propenal, 3-(4-hydroxy-2-methoxyphenyl)-；3-(4-hydroxy-2-methoxyphenyl)prop-2-enal
• CAS: 127321-19-1
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: MRCGVXARHKOYKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-methoxycinnamaldehyde 在 sodium tetrahydroborate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[3-[2-Methoxy-4-(4-phenylbutoxy)phenyl]prop-2-enylamino]propanoic acid
  参考文献：
  名称：

  Discovery of S1P agonists with a dihydronaphthalene scaffold

  摘要：

  Structure-activity relationship of sphingosine-1-phosphate receptor agonists was examined. Cinnamyl derivative 1 was modified to improve S1P(1) agonistic activity as well as selectivity over S1P(3) agonistic activity. Dihydronaphthalene derivative 10d was identified as a potent S1P(1) receptor agonist with high selectivity against S1P(3) and enhanced efficacy in lowering peripheral lymphocyte counts in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.029
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-hydroxy-2-methoxycinnamaldehyde
  参考文献：
  名称：

  Discovery of S1P agonists with a dihydronaphthalene scaffold

  摘要：

  Structure-activity relationship of sphingosine-1-phosphate receptor agonists was examined. Cinnamyl derivative 1 was modified to improve S1P(1) agonistic activity as well as selectivity over S1P(3) agonistic activity. Dihydronaphthalene derivative 10d was identified as a potent S1P(1) receptor agonist with high selectivity against S1P(3) and enhanced efficacy in lowering peripheral lymphocyte counts in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.029

文献信息

• Bioactive Aromatic Compounds from Leaves and Stems of <i>Vanilla fragrans</i>
  作者：Rongqi Sun、John N. Sacalis、Chee-Kok Chin、Cecil C. Still

  DOI：10.1021/jf010425k

  日期：2001.11.1

  and water were screened for toxic bioactivity against mosquito larvae. The results of these experiments showed that the fractions from the ethyl acetate and butanol phases were both active in the bioassay. Bioactivity of the ethyl acetate fraction was found to be much greater than that from the butanol fraction in mosquito larvae toxicity. The water phase appeared to contain no substances that impaired

  用乙酸乙酯和丁醇水溶液对香叶香草的叶和茎的酒精提取物进行分馏。筛选乙酸乙酯，丁醇和水的所有三个馏分，以对抗蚊子幼虫的毒性生物活性。这些实验的结果表明，来自乙酸乙酯和丁醇相的馏分在生物测定中均具有活性。发现在蚊虫幼虫毒性中，乙酸乙酯级分的生物活性远大于丁醇级分的生物活性。水相似乎不包含任何会损害蚊子幼虫生长的物质。在硅胶上对乙酸乙酯馏分进行反复柱色谱分离，分离出4-乙氧基甲基苯酚（1），4-丁氧基甲基苯酚（2），香兰素（3），4-羟基-2-甲氧基肉桂醛（4）和3,4 -二羟基苯基乙酸（5）。化合物4和5首次从香草物种中分离出来，尚未报道以天然形式发现2种化合物。主要成分为4-乙氧基甲基苯酚（1），但对蚊虫幼虫的毒性最强的是4-丁氧基甲基苯酚（2）。根据其质谱和（1）H或（13）C NMR数据确定化合物的结构。