(E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol | 110450-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol
• 英文别名: (E)-3-[3-methoxy-4-(methoxymethoxy)phenyl]prop-2-en-1-ol
• CAS: 110450-65-2
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: RGLIRNASKZDDHO-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 54.0h， 生成 4-Hydroxy-3-[(E)-3-(3-methoxy-4-methoxymethoxy-phenyl)-allyloxy]-benzaldehyde
  参考文献：
  名称：

  An Efficient Synthesis of 9-Oxaisotwist-8-en-2-ones. Synthesis of Deoxysilydianin Methyl Ether

  摘要：

  通过阳极氧化相应的苯酚这一关键步骤，脱氧雪莲苷甲醚很容易合成，这表明有一种高产率合成 9-氧代aisotwist-8-烯-2-酮的通用方法。

  DOI：

  10.1246/cl.1986.2097
• 作为产物：
  描述：

  阿魏酸 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol
  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

• Radical‐Cation Cascade to Aryltetralin Cyclic Ether Lignans Under Visible‐Light Photoredox Catalysis
  作者：Jia‐Chen Xiang、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202007548

  日期：2020.11.16

  concise, sustainable, and cost‐effective synthesis of aryltetralin lignans, bearing either a fused lactone or cyclic ether, is of significant medicinal importance. Reported is that in the presence of Fukuzumi's acridinium salt under blue LED irradiation, functionalized dicinnamyl ether derivatives are converted into aryltetralin cyclic ether lignans with concurrent generation of three stereocenters in

  开发具有稠合内酯或环状醚的简明，可持续且具有成本效益的芳基四氢呋喃木脂素合成具有重要的医学意义。据报道，在蓝色LED照射下在福住s啶鎓盐的存在下，功能化的二肉桂基醚衍生物被转化为芳基四氢环醚木脂素，同时以高至高收率同时生成了三个立体中心，非对映选择性高达20：1。烯烃氧化成自由基阳离子是电子不匹配的二烯和亲二烯体正式Diels-Alder反应成功的关键。应用这种方法，可以得到六种天然产物：Aglacin B，Aglacin C，sulabiroin A，sulabiroin B，gaultherin C和isoshonanin，从现成的生物质衍生的单木质醇仅需两到三个步骤即可合成。提出了针对高铁粘附素C的修订结构。
• Pauly; Feuerstein, Chemische Berichte, 1929, vol. 62, p. 303 Anm.18
  作者：Pauly、Feuerstein

  DOI：——

  日期：——
• Synthesis of Natural and Non-natural Curcuminoids and Their Neuroprotective Activity against Glutamate-Induced Oxidative Stress in HT-22 Cells
  作者：Petr Jirásek、Sabine Amslinger、Jörg Heilmann

  DOI：10.1021/np500396y

  日期：2014.10.24

  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.
• An Efficient Synthesis of 9-Oxaisotwist-8-en-2-ones. Synthesis of Deoxysilydianin Methyl Ether
  作者：Yoshikazu Shizuri、Hideyuki Shigemori、Yoshishige Okuno、Shosuke Yamamura

  DOI：10.1246/cl.1986.2097

  日期：1986.12.5

  Deoxysilydianin methyl ether has been readily synthesized by means of anodic oxidation of the corresponding phenol as a key step, indicating a general method for synthesis of 9-oxaisotwist-8-en-2-ones in high yields.

  通过阳极氧化相应的苯酚这一关键步骤，脱氧雪莲苷甲醚很容易合成，这表明有一种高产率合成 9-氧代aisotwist-8-烯-2-酮的通用方法。