(E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylaldehyde | 62427-71-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylaldehyde
• 英文别名: (E)-3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylaldehyde；(E)-3-(3-methoxy-4-methoxymethoxyphenyl)-2-propenal；3-methoxy-4-methoxymethoxy-cinnamaldehyde；3-Methoxy-4-methoxymethoxy-zimtaldehyd；(E)-3-[3-methoxy-4-(methoxymethoxy)phenyl]prop-2-enal
• CAS: 62427-71-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DSMOYXWZPJLKEI-ONEGZZNKSA-N

物化性质

• 沸点：
  373.9±37.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylaldehyde 在 硫酸 、 溶剂黄146 作用下， 生成 4-羟基-3-甲氧基肉桂醛
  参考文献：
  名称：

  Pauly; Feuerstein, Chemische Berichte, 1929, vol. 62, p. 303 Anm.18

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以69%的产率得到(E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylaldehyde
  参考文献：
  名称：

  Synthesis of Natural and Non-natural Curcuminoids and Their Neuroprotective Activity against Glutamate-Induced Oxidative Stress in HT-22 Cells

  摘要：

  A strategy for the synthesis of natural and non-natural 5-deoxy-6,7-dihydrocurcuminoids (diarylheptanoids) was developed for the preparation of 14 compounds with varying aromatic substituent patterns and a different functionality in the aliphatic seven-carbon chain. The in vitro protective activity against glutamate-induced neuronal cell death was examined in the murine hippocampal cell line HT-22 to find structural motifs responsible for neuroprotective effects in vitro. Among the tested compounds the ferulic acid-like unit, present in the structures of (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one (5) and (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-1-en-3-one (7), appeared to be an important feature for protection against glutamate-induced neurotoxicity. Both compounds demonstrated significant neuroprotective activity in a concentration range between 1 and 25 μM without showing toxic effects in a cytotoxicity assay with HT-22 cells. Furthermore, (E)-1,7-bis(3,4-dihydroxyphenyl)hept-1-en-3-one (9), exhibiting a caffeic acid-like structural motif, displayed a neuroprotective activity at a nontoxic concentration of 25 μM. In contrast, (1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione (4, di-O-demethylcurcumin) showed mainly cytotoxic effects. A corresponding single-ring analogue that contains the ferulic acid-like unit as an enone was not active.

  DOI：

  10.1021/np500396y

文献信息

• Scalable Total Synthesis of (+)- and (−)-Codonopiloneolignanin A via Ti(IV)/NHC Cooperative Control Highly Enantioselective Dimerization of Multisubstituted Cinnamaldehyde
  作者：Xiangxin Li、Huaya Yong、Xiaohong Fan、Yajuan Zheng、Zhen Wang、Zhixiang Xie

  DOI：10.1021/acs.orglett.1c02408

  日期：2021.8.20

  asymmetric total synthesis of (+)- and (−)-codonopiloneolignanin A has been achieved from multisubstituted cinnamaldehyde in four steps with 37% overall yield. The synthetically challenging tricyclic [5, 3, 0, 03,8] decane skeleton was efficiently constructed via a highly enantioselective dimerization of multisubstituted cinnamaldehyde, followed by a sequence of cascade reactions including Prins cyclization

  (+)-和(-)-codonopiloneolignanin A 的第一个克级不对称全合成已从多取代肉桂醛中分四步实现，总产率为 37%。具有挑战性的三环 [5, 3, 0, 0 3,8 ] 癸烷骨架是通过多取代肉桂醛的高度对映选择性二聚作用有效构建的，然后是一系列级联反应，包括 Prins 环化、阳离子介导的环化和脱保护。此外，研究了 NHC 催化/Ti(IV) 介导的协同控制多取代肉桂醛二聚的范围。重要的是，codonopiloneolignanin A 及其对映异构体的生物活性在自然界中特别稀缺，经测试并显示出良好的抗癌活性。
• Synthesis of 2-(4-Aryl-1E,3E-butadienyl)benzoxazoles by the Horner-Wadsworth-Emmons Reaction
  作者：Takatoshi Kosaka、Toshio Wakabayashi

  DOI：10.3987/com-94-6954

  日期：——

  2-(4-Aryl-1E,3E-butadienyl)benzoxazole derivatives were synthesized by the Horner-Wadsworth-Emmons reaction of 2-phosphorylmethyl-benzoxazoles with cinnamaldehydes in fair to good yield.
• Kosaka,Takatoshi; Ochiai, Keiko; Wakabayashi, Toshio, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 502 - 514
  作者：Kosaka,Takatoshi、Ochiai, Keiko、Wakabayashi, Toshio、Murota, Sei-itsu

  DOI：——

  日期：——
• Kobayashi, Scientific Papers of the Institute of Physical and Chemical Research (Japan), vol. 6, p. 182
  作者：Kobayashi

  DOI：——

  日期：——
• Pauly; Waescher, Chemische Berichte, 1923, vol. 56, p. 607
  作者：Pauly、Waescher

  DOI：——

  日期：——