6,8-bis(phenylmethoxy)-4H-isochromene-1,3-dione | 790699-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,8-bis(phenylmethoxy)-4H-isochromene-1,3-dione
• CAS: 790699-37-5
• 化学式: C₂₃H₁₈O₅
• 分子量: 374.393
• InChiKey: HIWSLPRIRYPJTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,8-bis(phenylmethoxy)-4H-isochromene-1,3-dione 在 palladium dihydroxide 4 A molecular sieve 、 TEA 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 (3R)-6,8,9-trihydroxy-2-(1-hydroxyhexyl)-3-methyl-3,4-dihydro-2H-anthracen-1-one
  参考文献：
  名称：

  New DNA binding ligands as a model of chromomycin A3

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A(3) (CRA(3)) which contains a hydroxylated tetrahydroanthracene chromophore substituted with di and trisaccharides. The trisaccharide part of CRA(3) that is supposed to contribute to form the Mg2+-coordinated dimer was expected to be mimicked by a simple alkyl group attached to the chromophore part as new model compounds. The present study has successfully demonstrated that the new ligands form Mg2+-coordinated dimer complexes to exhibit DNA-binding affinity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.043
• 作为产物：
  描述：

  3,5-dibenzyloxyhomophthalic acid 在 (乙氧基乙炔基)(三甲基)硅烷 作用下， 以91%的产率得到6,8-bis(phenylmethoxy)-4H-isochromene-1,3-dione
  参考文献：
  名称：

  New DNA binding ligands as a model of chromomycin A3

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A(3) (CRA(3)) which contains a hydroxylated tetrahydroanthracene chromophore substituted with di and trisaccharides. The trisaccharide part of CRA(3) that is supposed to contribute to form the Mg2+-coordinated dimer was expected to be mimicked by a simple alkyl group attached to the chromophore part as new model compounds. The present study has successfully demonstrated that the new ligands form Mg2+-coordinated dimer complexes to exhibit DNA-binding affinity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.043

文献信息

• Stereoselective synthesis of (+)-2-deoxyolivin based on cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivative
  作者：Yoshinari Haruta、Kazumitsu Onizuka、Kyouichi Watanabe、Kyoko Kono、Akihiro Nohara、Kenichi Kubota、Shuhei Imoto、Shigeki Sasaki

  DOI：10.1016/j.tet.2008.05.080

  日期：2008.7

  tricyclic aglycon core, olivin. In this study, we established the efficient synthesis of the anthracenone core skeleton based on a cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivatives, which is promoted by the combined use of molecular sieves, proton sponge, and a Lewis acid. The cyclohexenone with four chiral centers was synthesized by asymmetric and diastereoselective

  olivomycins是该化合物的aureolic家族中的代表性抗肿瘤抗生素，其包含三环糖苷配基核心olivin。在这项研究中，我们建立了基于间苯二甲酸酐与手性环己烯酮衍生物之间的环加成反应的蒽环核心骨架的有效合成方法，该反应可通过分子筛，质子海绵和路易斯酸的组合使用而得到促进。通过不对称和非对映选择性反应合成具有四个手性中心的环己烯酮，并使其与高邻苯二甲酸酐进行环加成反应，然后进行一系列反应以完成（+）-2-脱氧低聚香醇的立体选择性合成。
• New DNA binding ligands as a model of chromomycin A3
  作者：Shuhei Imoto、Yoshinari Haruta、Kyouichi Watanabe、Shigeki Sasaki

  DOI：10.1016/j.bmcl.2004.07.043

  日期：2004.10

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A(3) (CRA(3)) which contains a hydroxylated tetrahydroanthracene chromophore substituted with di and trisaccharides. The trisaccharide part of CRA(3) that is supposed to contribute to form the Mg2+-coordinated dimer was expected to be mimicked by a simple alkyl group attached to the chromophore part as new model compounds. The present study has successfully demonstrated that the new ligands form Mg2+-coordinated dimer complexes to exhibit DNA-binding affinity. (C) 2004 Elsevier Ltd. All rights reserved.