3,5-dibenzyloxyhomophthalic acid | 96864-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dibenzyloxyhomophthalic acid
• 英文别名: 2,4-bis-benzyloxy-6-carboxymethylbenzoic acid methyl ester；2-(Carboxymethyl)-4,6-bis(phenylmethoxy)benzoic acid
• CAS: 96864-17-4
• 化学式: C₂₃H₂₀O₆
• 分子量: 392.408
• InChiKey: AHYAZHBHOSIAHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  dimethyl 3,5-dihydroxyhomophthalate 在 氢氧化钾 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 72.0h， 生成 3,5-dibenzyloxyhomophthalic acid
  参考文献：
  名称：

  4-乙酰基异香豆素的合成：首先是AGI-7和sescandelin的全合成。

  摘要：

  描述了一种实用的合成4-乙酰基异香豆素的途径，以及AGI-7（5）和sescandelin（4）的第一个全合成。容易获得的高邻苯二甲酸酯8以高的总收率转化成乙烯基酰胺酯13。用回流的甲酸水溶液处理13时，以3∶1的比例产生所需的4-乙酰基异香豆素（5）及其区域异构体3-甲基-4-甲酰基异香豆素（17）。从不需要的次要异构体中分离出所需产物（5）后，在Corey's（S）-恶唑硼烷试剂存在下，硼烷将AGI-7对映选择性还原，得到（93）ee的（+）-sescandelin（4）。

  DOI：

  10.1021/jo010789b

文献信息

• Synthesis of 4-Acetylisocoumarin:  First Total Syntheses of AGI-7 and Sescandelin
  作者：Sanghee Kim、Gao-jun Fan、Jaekwang Lee、Jung Joon Lee、Deukjoon Kim

  DOI：10.1021/jo010789b

  日期：2002.5.1

  A practical synthetic route to 4-acetylisocoumarins and the first total synthesis of AGI-7 (5) and sescandelin (4) are described. The readily available homophthalate 8 was transformed to the vinylogous amide ester 13 in high overall yield. Upon treatment of 13 with refluxing aqueous formic acid, the desired 4-acetylisocoumarin (5) and its regioisomer 3-methyl-4-formylisocoumarin (17) were produced

  描述了一种实用的合成4-乙酰基异香豆素的途径，以及AGI-7（5）和sescandelin（4）的第一个全合成。容易获得的高邻苯二甲酸酯8以高的总收率转化成乙烯基酰胺酯13。用回流的甲酸水溶液处理13时，以3∶1的比例产生所需的4-乙酰基异香豆素（5）及其区域异构体3-甲基-4-甲酰基异香豆素（17）。从不需要的次要异构体中分离出所需产物（5）后，在Corey's（S）-恶唑硼烷试剂存在下，硼烷将AGI-7对映选择性还原，得到（93）ee的（+）-sescandelin（4）。
• Kjaer, Anders; Kjaer, Dana, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 1, p. 65 - 68
  作者：Kjaer, Anders、Kjaer, Dana

  DOI：——

  日期：——
• 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.