1,2,4,5-tetrakis((methoxy)methoxy)-3,6-dibromobenzene | 1160726-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,4,5-tetrakis((methoxy)methoxy)-3,6-dibromobenzene
• 英文别名: 1,4-Dibromo-2,3,5,6-tetrakis(methoxymethoxy)benzene
• CAS: 1160726-15-7
• 化学式: C₁₄H₂₀Br₂O₈
• 分子量: 476.116
• InChiKey: WVGPSZNQDUAPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrakis((methoxy)methoxy)-3,6-dibromobenzene 在 potassium phosphate 、 ammonium cerium (IV) nitrate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4,4''-bis((tert-butyldimethylsilyl)oxy)-3',6'-bis(methoxymethoxy)-[1,1':4',1''-terphenyl]-2',5'-dione
  参考文献：
  名称：

  Structural revision of kynapcin-12 by total synthesis, and inhibitory activities against prolyl oligopeptidase and cancer cells

  摘要：

  Kynapcin-12 is a prolyl oligopeptidase (POP) inhibitor isolated from Polyozellus multiplex, and its structure was assigned as 1 having a p-hydroquinone moiety by spectroscopic analyses and chemical means. This Letter describes the total syntheses of the proposed structure 1 for kynapcin-12 and 2',3'-diacetoxy-1,5',6',4 ''-tetrahydroxy-p-terphenyl 2 isolated from Boletopsis grisea, revising the structure of kynapcin-12 to the latter. These syntheses involved double Suzuki-Miyaura coupling, CAN oxidation, and LTA oxidation as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.091
• 作为产物：
  描述：

  tetrahydroxy-p-bromobenzene 、 氯甲基甲基醚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.33h， 以3.96 g的产率得到1,2,4,5-tetrakis((methoxy)methoxy)-3,6-dibromobenzene
  参考文献：
  名称：

  全合成合成鞘磷脂G的结构修饰及其对TNF-α产生的抑制活性

  摘要：

  本文描述了鞘磷脂G的全合成，从而将提出的结构1修改为2。关键步骤涉及Suzuki-Miyaura双偶联和酯化反应。通过类似的策略，还制备了ganbajunins D和E（3和4）。化合物2强烈抑制大鼠嗜碱性白血病（RBL-2H3）细胞中TNF（肿瘤坏死因子）-α的产生：IC 50 = 3.5 nM，而1和其区域异构体15的混合物则没有这种活性。

  DOI：

  10.1021/jo900638b

文献信息

• Structural Revision of Thelephantin G by Total Synthesis and the Inhibitory Activity against TNF-α Production
  作者：Yue Qi Ye、Hiroyuki Koshino、Jun-ichi Onose、Chiemi Negishi、Kunie Yoshikawa、Naoki Abe、Shunya Takahashi

  DOI：10.1021/jo900638b

  日期：2009.6.19

  This paper describes the total synthesis of thelephantin G, thus revising the proposed structure 1 to 2. The key steps involved a double Suzuki−Miyaura coupling and an esterification reaction. By a similar strategy, ganbajunins D and E (3 and 4) were also prepared. Compound 2 strongly inhibited TNF (tumor necrosis factor)-α production in rat basophilic leukemia (RBL-2H3) cells: IC50 = 3.5 nM, while

  本文描述了鞘磷脂G的全合成，从而将提出的结构1修改为2。关键步骤涉及Suzuki-Miyaura双偶联和酯化反应。通过类似的策略，还制备了ganbajunins D和E（3和4）。化合物2强烈抑制大鼠嗜碱性白血病（RBL-2H3）细胞中TNF（肿瘤坏死因子）-α的产生：IC 50 = 3.5 nM，而1和其区域异构体15的混合物则没有这种活性。
• Structural revision of kynapcin-12 by total synthesis, and inhibitory activities against prolyl oligopeptidase and cancer cells
  作者：Shunya Takahashi、Ayaka Yoshida、Shota Uesugi、Yayoi Hongo、Ken-ichi Kimura、Koji Matsuoka、Hiroyuki Koshino

  DOI：10.1016/j.bmcl.2014.05.091

  日期：2014.8

  Kynapcin-12 is a prolyl oligopeptidase (POP) inhibitor isolated from Polyozellus multiplex, and its structure was assigned as 1 having a p-hydroquinone moiety by spectroscopic analyses and chemical means. This Letter describes the total syntheses of the proposed structure 1 for kynapcin-12 and 2',3'-diacetoxy-1,5',6',4 ''-tetrahydroxy-p-terphenyl 2 isolated from Boletopsis grisea, revising the structure of kynapcin-12 to the latter. These syntheses involved double Suzuki-Miyaura coupling, CAN oxidation, and LTA oxidation as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated. (C) 2014 Elsevier Ltd. All rights reserved.