3-Benzoyl-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one | 263902-83-6

• 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: 3-Benzoyl-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one
• 英文别名: 3-Benzoyl-8,8-dimethylpyrano[2,3-f]chromen-2-one；3-benzoyl-8,8-dimethylpyrano[2,3-f]chromen-2-one
• CAS: 263902-83-6
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: FTJJFBZTCWFRAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one 在 Amberlyst-15 (H⁺) resin 、 polymer-bound 4-(N-benzyl-N-methylamino)pyridine 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 13.5h， 生成 Acetic acid (9R,10S)-3-benzoyl-10-ethoxy-8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-9-yl ester
  参考文献：
  名称：

  Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The “Libraries from Libraries” Principle for Diversity Enhancement of Benzopyran Libraries

  摘要：

  As described in the preceding two papers, our interest in the construction of natural and natural product-like libraries for chemical biology studies led to the development of a new solid-phase cycloloading strategy for the construction of substituted benzopyrans. Herein, we report a parallel solution-phase method that facilitates the enhancement of both the size and diversity of these non-oligomeric benzopyran libraries using the "libraries from libraries" principle. We examine the rationale behind the use of this tandem strategy to construct discrete small molecule libraries, and describe the development of a polymer-assisted solution-phase (PASP) methodology necessary to effect the required transformations. Once developed, this chemistry is applied to two demonstration libraries.

  DOI：

  10.1021/ja0020355
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 、 2,4-dihydroxy-3-(3-methyl-2-but-en-1-yl)benzaldehyde 在 selenium bromide polystyrene resin 、 哌啶 、 双氧水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.0h， 以89%的产率得到3-Benzoyl-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  苯并吡喃的硒基固相合成 I：在天然产物组合合成中的应用

  摘要：

  DOI：

  10.1002/(sici)1521-3773(20000218)39:4<734::aid-anie734>3.0.co;2-i

文献信息

• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Selenium-Based Solid-Phase Synthesis of Benzopyrans I: Applications to Combinatorial Synthesis of Natural Products
  作者：K. C. Nicolaou、Jeffrey A. Pfefferkorn、Guo-Qiang Cao

  DOI：10.1002/(sici)1521-3773(20000218)39:4<734::aid-anie734>3.0.co;2-i

  日期：2000.2.18
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The “Libraries from Libraries” Principle for Diversity Enhancement of Benzopyran Libraries
  作者：K. C. Nicolaou、J. A. Pfefferkorn、S. Barluenga、H. J. Mitchell、A. J. Roecker、G.-Q. Cao

  DOI：10.1021/ja0020355

  日期：2000.10.1

  As described in the preceding two papers, our interest in the construction of natural and natural product-like libraries for chemical biology studies led to the development of a new solid-phase cycloloading strategy for the construction of substituted benzopyrans. Herein, we report a parallel solution-phase method that facilitates the enhancement of both the size and diversity of these non-oligomeric benzopyran libraries using the "libraries from libraries" principle. We examine the rationale behind the use of this tandem strategy to construct discrete small molecule libraries, and describe the development of a polymer-assisted solution-phase (PASP) methodology necessary to effect the required transformations. Once developed, this chemistry is applied to two demonstration libraries.