3-methoxy-4,5-bis(methoxymethoxy)benzaldehyde | 297132-89-9

• 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: 3-methoxy-4,5-bis(methoxymethoxy)benzaldehyde
• 英文别名: 3-methoxy-4,5-dimethoxymethoxybenzaldehyde；Benzaldehyde, 3-methoxy-4,5-bis(methoxymethoxy)-
• CAS: 297132-89-9
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: WYOBUVRFMPXKBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methoxy-4,5-bis(methoxymethoxy)benzaldehyde 在 盐酸 、 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 65.33h， 生成 5,7,3',4'-tetrahydroxy-5'-methoxyflavone,
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d
• 作为产物：
  描述：

  3,4-二羟基-5-甲氧基苯甲醛 、 氯甲基甲基醚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以85%的产率得到3-methoxy-4,5-bis(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans

  摘要：

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.

  DOI：

  10.1021/np000166d

文献信息

• Discovery of novel (1S)-(−)-verbenone derivatives with anti-oxidant and anti-ischemic effects
  作者：Chung Ju、Sumi Song、Sunyoung Hwang、Chorong Kim、Minkyoung Kim、Jail Gu、Yu-Kyoung Oh、Kyeong Lee、Jinsun Kwon、Kiho Lee、Won-Ki Kim、Yongseok Choi

  DOI：10.1016/j.bmcl.2013.07.038

  日期：2013.10

  A series of novel (1S)-(−)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen–glucose deprivation-induced neuronal injury and N-methyl-d-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore, compound 3f was identified

  合成了一系列带有4-苯乙烯基支架的新颖的（1 S）-（-）-马来酮衍生物。测试了合成的化合物的抗氧化，抗兴奋毒性和抗缺血活性。这些衍生物显著降低的氧气-葡萄糖剥夺诱导的神经元损伤和Ñ甲基d在皮层神经元-天冬氨酸诱发的兴奋毒性。此外，化合物3F被鉴定为在体外缺血模型有效的抗局部缺血剂，这可能是由于抑制Ñ甲基d天冬氨酸诱发的兴奋性毒性和氧化/亚硝化应激。
• Synthesis and Structures of Regioisomeric Hydnocarpin-Type Flavonolignans
  作者：Nathan R. Guz、Frank R. Stermitz

  DOI：10.1021/np000166d

  日期：2000.8.1

  Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.