2,5-diallyloxybenzaldehyde | 103811-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-diallyloxybenzaldehyde
• 英文别名: 2,5-Bis(prop-2-enoxy)benzaldehyde
• CAS: 103811-70-7
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: CLOKIYZKEMUQTE-UHFFFAOYSA-N

物化性质

• 沸点：
  348.2±32.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-diallyloxybenzaldehyde 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 sodium hydride 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 氯仿 为溶剂， 反应 150.5h， 生成 (+/-)-(4aS,4bR,8aS,9R)-9-(2,5-dimethylphenyl)-8a-[(E)-2-(2,5-dimethylphenyl)ethenyl]-4a,4b,8a,9-tetrahydrophenanthrene-1,4,5,8-tetrone
  参考文献：
  名称：

  1,4-Benzoquinones with Styryl Substituents

  摘要：

  2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4pi + 2pi] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1-10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 --> 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4pi + 2pi] cycloaddition (10 --> 11). The same selective [4pi + 2pi] cyclodimerization can be observed in solution upon irradiation (e.g., 1a --> 10a), in contrast to irradiation in the crystalline state which yields a [2pi + 2pi] dimer (e.g., 1a --> 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1-3) and 3a (n = 1-4) are obtained. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200209)2002:18<3162::aid-ejoc3162>3.0.co;2-h
• 作为产物：
  描述：

  [2,5-bis(prop-2-enoxy)phenyl]methanol 生成 2,5-diallyloxybenzaldehyde
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Antileishmanial Chalcones:  Statistical Design, Synthesis, and Three-Dimensional Quantitative Structure−Activity Relationship Analysis
  作者：Simon Feldbæk Nielsen、Søren Brøgger Christensen、Gabriele Cruciani、Arsalan Kharazmi、Tommy Liljefors

  DOI：10.1021/jm980410m

  日期：1998.11.1

  coefficient plots indicate that steric interactions between the chalcones and the target are of major importance for the potencies of the compounds. A comparison of the coefficient plots for the antileishmanial effect and the lymphocyte-suppressing activity discloses significant differences which should make it possible to design chalcones having a high antileishmanial activity without suppressing the

  已经合成了大量取代的查耳酮，并测试了其对抗盲肠和淋巴细胞的抑制活性。使用统计方法设计了查耳酮的一个子集。通过使用GRID / GOLPE方法，使用67种化合物（抗肠蠕动活性）和63种化合物（抑制淋巴细胞的活性）对训练组和9种化合物作为外部验证组进行了3D-QSAR分析。在GOLPE中实施的具有区域选择功能的智能区域定义程序将变量数量减少到大约1300个，从而产生了高质量的3D-QSAR模型（​​淋巴细胞抑制模型，R2 =0。90，Q2 = 0.80；反兽皮模型，R2 = 0.73，Q2 = 0.63）。系数图表明，查耳酮与靶标之间的空间相互作用对于化合物的效能至关重要。抗菌剂作用和淋巴细胞抑制活性的系数图的比较揭示了显着的差异，这应该使设计具有高抗菌剂活性的查耳酮成为可能，而又不抑制淋巴细胞的增殖。
• TRIPHENYLPHOSPHONIUM-TETHERED SALICYLAMINE DERIVATIVES
  申请人：MTI BIOTECH, INC.

  公开号：US20220112152A1

  公开（公告）日：2022-04-14

  Novel salicylamine derivatives are targeted directly to the mitochondria to increase effectiveness and lower required dosages in the treatment of conditions caused by inflammation or oxidative stress.

  新型水杨酰胺衍生物直接针对线粒体，以增强效果并降低治疗由炎症或氧化应激引起的疾病所需的剂量。
• ——
  作者：FINCH M. A. W.、 HARRIS J. R.

  DOI：——

  日期：——
• [EN] TRIPHENYLPHOSPHONIUM-TETHERED SALICYLAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE SALICYLAMINE LIÉS AU TRIPHÉNYLPHOSPHONIUM
  申请人：MTI BIOTECH INC

  公开号：WO2020154731A1

  公开（公告）日：2020-07-30

  Novel salicylamine derivatives are targeted directly to the mitochondria to increase effectiveness and lower required dosages in the treatment of conditions caused by inflammation or oxidative stress.
• 1,4-Benzoquinones with Styryl Substituents
  作者：Isabella Brehm、Sabine Hinneschiedt、Herbert Meier

  DOI：10.1002/1099-0690(200209)2002:18<3162::aid-ejoc3162>3.0.co;2-h

  日期：2002.9

  2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4pi + 2pi] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1-10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 --> 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4pi + 2pi] cycloaddition (10 --> 11). The same selective [4pi + 2pi] cyclodimerization can be observed in solution upon irradiation (e.g., 1a --> 10a), in contrast to irradiation in the crystalline state which yields a [2pi + 2pi] dimer (e.g., 1a --> 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1-3) and 3a (n = 1-4) are obtained. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).