[3,5-二(丙烷-2-氧基)苯基]甲醇 | 94169-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: [3,5-二(丙烷-2-氧基)苯基]甲醇
• 英文名称: (3,5-diisopropoxyphenyl)methanol
• 英文别名: [3,5-di(propan-2-yloxy)phenyl]methanol
• CAS: 94169-63-8
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: HLIPDPDFDSHIGX-UHFFFAOYSA-N

物化性质

• 沸点：
  342.7±27.0 °C(Predicted)
• 密度：
  1.028±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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  [3,5-二(丙烷-2-氧基)苯基]甲醇 在 氢氧化钾 、 磷酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-(3,5-Diisopropoxy-phenyl)-5,7-diisopropoxy-chroman-4-one
  参考文献：
  名称：

  Huazhongilexone is not 3',5,5',7-Tetrahydroxyflavanone. Preparation of 3',5'-Dimethoxy-5,7-dihydroxyflavanone.

  摘要：

  Huazhongilexone, isolated from Ilex centrochinensis, was originally assigned the structure 3 ',5,5 ',7-tetrahydroxyflavanone. The racemic flavanone has been synthezised. Huazhongilexone is different from the synthetic compound and thus must have a different structure. In addition the new (+/-)-3 ',5 '-dimethoxy-5,7-dihydroxyflavanone has been prepared and characterized.

  DOI：

  10.3891/acta.chem.scand.52-1243
• 作为产物：
  描述：

  3,5-二异丙氧基苯甲酸异丙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到[3,5-二(丙烷-2-氧基)苯基]甲醇
  参考文献：
  名称：

  噬菌体A的半噬菌体-AB片段的改良合成

  摘要：

  需要金绿宝石蛋白A（一种罕见的抗菌海洋天然产物）的合成片段来支持结构活性和作用机理研究。金丝雀蛋白A的合成片段半金丝雀蛋白显示出对革兰氏阳性细菌的抗菌活性，大概是通过抑制微生物微管蛋白样蛋白FtsZ发挥作用。在本文中，我们报告了半透明的phaphrystent的简洁且可扩展的11个步骤的合成，其特征在于立体和区域控制的E-氯代烯烃的安装，然后路易斯酸促进了O到C的迁移。

  DOI：

  10.1016/j.tetlet.2020.151856

文献信息

• Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
  作者：Jan Šmidrkal、Juraj Harmatha、Miloš Buděšínský、Karel Vokáč、Zdeněk Zídek、Eva Kmoníčková、Roman Merkl、Vladimír Filip

  DOI：10.1135/cccc2009531

  日期：——

  Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed asE-isomers only (using Wittig–Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-γ were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.

  白藜芦醇及其密切相关的蒽醌类化合物属于研究最为深入的生物活性化合物之一。这种兴趣引发了几次尝试以便利的合成方式制备这类化合物。我们的方法允许获得大量的甲氧基蒽醌类化合物，仅形成E-异构体（使用Wittig-Horner合成作为关键步骤），随后通过三溴化硼进行去甲基化。羟甲氧基蒽醌类化合物（例如蓝莓素）采用异丙基保护制备，后来通过三氯化硼进行选择性去保护。该方法适用于大量制备这类化合物。在体外条件下测试了所获得的蒽醌衍生物对脂多糖和干扰素-γ引发的免疫生物学反应的影响。具体而言，研究了一氧化氮（NO）的产生，并评估了分子结构与免疫生物学活性之间的关系。
• Conformational Effects on the Threading Kinetics of Dumbbell‐Shaped Guests into the Cavity of Oxatub[4]arene
  作者：Fei Jia、Dong‐Hao Li、Shan He、Liu‐Pan Yang、Wei Jiang

  DOI：10.1002/anie.202212305

  日期：2022.11.7

  observed in a two-component system containing a viologen-based guest and oxatub[4]arene through the involvement of the three conformers of the host. In addition, an unprecedented threading mechanism involving the tilted conformation of the guests was revealed to be responsible for the very fast kinetics and for the threading of guests with very large stoppers.

  通过宿主的三个构象异构体的参与，在一个包含紫罗碱基客体和氧杂蒽酮 [4] 芳烃的双组分系统中观察到复杂的动力学行为。此外，一种前所未有的涉及客体倾斜构造的穿线机制被揭示为非常快速的动力学和具有非常大的塞子的客体穿线的原因。
• Chiral Auxiliary Approach for Gold(I)‐Catalyzed Cyclizations
  作者：Andrea Cataffo、Miguel Peña‐López、Riccardo Pedrazzani、Antonio M. Echavarren

  DOI：10.1002/anie.202312874

  日期：2023.12.4

  The stereoselective gold(I)-catalyzed cascade cyclization of 1,5-enynes and alkoxycyclization of 1,6-enynes with chiral auxiliaries has been developed, affording, after hydrolysis, synthetically challenging enantioenriched ketones. This chiral auxiliary approach is an alternative to the use of complex chiral catalysts in gold(I)-catalyzed asymmetric cyclizations.

  已经开发出立体选择性金 (I) 催化的 1,5-烯炔级联环化和 1,6-烯炔与手性助剂的烷氧基环化，在水解后提供合成上具有挑战性的对映体富集酮。这种手性辅助方法是金 (I) 催化不对称环化中使用复杂手性催化剂的替代方法。
• Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2
  作者：Sarah E. St. John、Katherine C. Jensen、SooSung Kang、Yafang Chen、Barbara Calamini、Andrew D. Mesecar、Mark A. Lipton

  DOI：10.1016/j.bmc.2013.07.037

  日期：2013.10

  Resveratrol (3,5,4'-trihydroxylstilbene) has been proposed to elicit a variety of positive health effects including protection against cancer and cardiovascular disease. The highest affinity target of resveratrol identified so far is the oxidoreductase enzyme quinone reductase 2 (QR2), which is believed to function in metabolic reduction and detoxification processes; however, evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Therefore, inhibition of QR2 by resveratrol may protect cells against reactive intermediates and eventually cancer. With the aim of identifying novel inhibitors of QR2, we designed, synthesized, and tested two generations of resveratrol analogue libraries for inhibition of QR2. In addition, Xray crystal structures of six of the resveratrol analogues in the active site of QR2 were determined. Several novel inhibitors of QR2 were successfully identified as well as a compound that inhibits QR2 with a novel binding orientation. (c) 2013 Elsevier Ltd. All rights reserved.
• Sargent, Melvyn V.; Stanojevic, Edi, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1919 - 1921
  作者：Sargent, Melvyn V.、Stanojevic, Edi

  DOI：——

  日期：——