6,8-di-tert-butyl-4-hydroxycoumarin | 1043964-22-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,8-di-tert-butyl-4-hydroxycoumarin
• 英文别名: 6,8-Ditert-butyl-4-hydroxychromen-2-one
• CAS: 1043964-22-2
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: IRKLPQAAHPCJPS-UHFFFAOYSA-N

物化性质

• 熔点：
  262.2-263.5 °C
• 沸点：
  389.7±42.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-di-tert-butyl-4-hydroxycoumarin 在 三氯氧磷 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-((6,8-di-tert-butyl-4-chloro-2-oxo-2H-chromen-3-yl)methyleneamino)benzenesulfonamide
  参考文献：
  名称：

  Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

  摘要：

  A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 51 (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.035
• 作为产物：
  描述：

  2,4-二叔丁基苯酚 在 eaton’s reagent 作用下， 反应 7.0h， 生成 6,8-di-tert-butyl-4-hydroxycoumarin
  参考文献：
  名称：

  清洁方便的 4-羟基香豆素和 4-羟基-2-喹啉酮衍生物的一锅法合成

  摘要：

  以伊顿试剂（磷酸酐+甲基磺酸）为环化试剂，Meldrum 酸与苯酚、取代苯酚、苯胺或取代苯胺反应，已开发出一种简单、高效且环保的方法。4-羟基香豆素和4-羟基-2-喹啉酮类化合物在无溶剂、方便、清洁的一锅法制备中以中等收率合成。

  DOI：

  10.1080/00397910903013713

文献信息

• Enantioselective Synthesis of Polycyclic Coumarin Derivatives Catalyzed by an <i>in Situ</i> Formed Primary Amine-Imine Catalyst
  作者：Xi Zhu、Aijun Lin、Yan Shi、Jingyu Guo、Chengjian Zhu、Yixiang Cheng

  DOI：10.1021/ol201715h

  日期：2011.8.19

  A facile in situ formed primary amine-imine organocatalyst was developed in the asymmetric Michael addition of substituted 4-hydroxycoumarins to cyclic enones. A series of optically active polycyclic coumarin derivatives were obtained in high yields with excellent enantioselectivities up to 97% ee.

  在取代的4-羟基香豆素向环烯酮的不对称迈克尔加成反应中，开发了一种简便的原位形成的伯胺-亚胺有机催化剂。以高收率获得了一系列光学活性的多环香豆素衍生物，其对映体选择性高达97％ee。
• Regioselective <scp>Bismuth‐Catalyzed</scp> Synthesis of Pyranocoumarins and Furocoumarins from <scp>4‐Hydroxycoumarins</scp> and Propargyl Alcohols
  作者：Jaehyun Kim、Kooyeon Lee、Phil Ho Lee

  DOI：10.1002/bkcs.12058

  日期：2020.7

  An efficient method for the bismuth‐catalyzed regioselective synthesis of pyranocoumarins and furocoumarins has been developed from the reaction of 4‐hydroxycoumarins with propargyl alcohols. The reaction proceeds through sequential propargylation and intramolecular cyclization reactions catalyzed by bismuth(III) triflate.

  4-羟基香豆素与炔丙醇的反应已开发出一种高效的铋催化吡喃香豆素和呋喃香豆素的区域选择性合成方法。该反应通过三氟甲磺酸铋（III）催化的顺序炔丙基化和分子内环化反应进行。