1-(3,4-dimethoxyphenyl)-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propan-1-one | 68143-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4-dimethoxyphenyl)-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propan-1-one
• 英文别名: 3,4-dimethoxy-8-[3'-methoxy-4'-(E)-propenylphenoxy]propiophenone；Oxovirolin；1-(3,4-dimethoxyphenyl)-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]propan-1-one
• CAS: 68143-86-2
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: IQQVVIZXMFMANE-VOTSOKGWSA-N

物化性质

• 沸点：
  520.0±50.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propan-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以385 mg的产率得到1-(3,4-dimethoxyphenyl)-2-[2-methoxy-4-[(E)-prop-1-enyl]phenoxy]propan-1-ol
  参考文献：
  名称：

  In Vitro Evaluation of Antifungal Properties of 8.O.4‘-Neolignans

  摘要：

  Eighteen racemic 8.O.4'-neolignans with six different substitution patterns in rings A and B, in their ketone and in their erythro and three alcoholic forms, were evaluated for antifungal activity by the agar dilution method. Only the alcohols exhibited a broad spectrum of activities against Microsporum canis, Microsporum gypseum, Tricophyton mentagrophytes, Tricophyton rubrum, and Epidermophyton floccosum. (+/-)-erythro-3,4-(methylenedioxy)-7-hydroxy-1'-allyl-3'5'-dimethoxy-8.O.4'-neolignan (11) was the most active compound in the series, and E. floccosum was the most susceptible species.

  DOI：

  10.1021/np9605504
• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 2-溴-3-4-二甲氧基苯丙酮 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 以81%的产率得到1-(3,4-dimethoxyphenyl)-2-{2-methoxy-4-[(1E)-prop-1-en-1-yl]phenoxy}propan-1-one
  参考文献：
  名称：

  Structure–activity relationship of antileishmanials neolignan analogues

  摘要：

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.016

文献信息

• Neolignans of Virola surinamensis
  作者：Lauro E.S. Barata、Paul M. Baker、Otto R. Gottlieb、Edmundo A. Rùveda

  DOI：10.1016/s0031-9422(00)94227-4

  日期：1978.1
• Structure–activity relationship of antileishmanials neolignan analogues
  作者：Mário Aveniente、Eduardo F. Pinto、Lourivaldo S. Santos、Bartira Rossi-Bergmann、Lauro E.S. Barata

  DOI：10.1016/j.bmc.2007.08.016

  日期：2007.12

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.
• In Vitro Evaluation of Antifungal Properties of 8.O.4‘-Neolignans
  作者：Susana Zacchino、Gladis Rodríguez、Germán Pezzenati、Gabriela Orellana、Ricardo Enriz、Manuel Gonzalez Sierra

  DOI：10.1021/np9605504

  日期：1997.7.1

  Eighteen racemic 8.O.4'-neolignans with six different substitution patterns in rings A and B, in their ketone and in their erythro and three alcoholic forms, were evaluated for antifungal activity by the agar dilution method. Only the alcohols exhibited a broad spectrum of activities against Microsporum canis, Microsporum gypseum, Tricophyton mentagrophytes, Tricophyton rubrum, and Epidermophyton floccosum. (+/-)-erythro-3,4-(methylenedioxy)-7-hydroxy-1'-allyl-3'5'-dimethoxy-8.O.4'-neolignan (11) was the most active compound in the series, and E. floccosum was the most susceptible species.