4,4''-bis((tert-butyldimethylsilyl)oxy)-3',6'-bis(methoxymethoxy)-[1,1':4',1''-terphenyl]-2',5'-dione | 1263406-89-8

• 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: 4,4''-bis((tert-butyldimethylsilyl)oxy)-3',6'-bis(methoxymethoxy)-[1,1':4',1''-terphenyl]-2',5'-dione
• CAS: 1263406-89-8
• 化学式: C₃₄H₄₈O₈Si₂
• 分子量: 640.921
• InChiKey: FUUQWSGFKXMSQG-UHFFFAOYSA-N

物化性质

• 沸点：
  659.5±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4,4''-bis((tert-butyldimethylsilyl)oxy)-3',6'-bis(methoxymethoxy)-[1,1':4',1''-terphenyl]-2',5'-dione 、 乙酰氯 在 sodium dithionite 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 以91%的产率得到4,4''-bis((tert-butyldimethylsilyl)oxy)-3',6'-bis(methoxymethoxy)-[1,1':4',1''-terphenyl]-2',5'-diyl diacetate
  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：

  ((2',3',5',6'-tetrakis(methoxymethoxy)-[1,1':4',1''-terphenyl]-4,4''-diyl)bis(oxy))bis(tert-butyldimethylsilane) 在 ammonium cerium (IV) nitrate 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