4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole-5,6-dione | 956024-13-8

• 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: 4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole-5,6-dione
• 英文别名: 4,7-bis-(p-(t-butyldimethylsilyloxy)phenyl)benzo[1,3]dioxole-5,6-dione；4,7-Bis[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-1,3-benzodioxole-5,6-dione
• CAS: 956024-13-8
• 化学式: C₃₁H₄₀O₆Si₂
• 分子量: 564.826
• InChiKey: UTRGLMUGDWSTTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole-5,6-dione 在 盐酸 、 正丁基锂 、 sodium dithionite 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 71.83h， 生成 4,4'',5',6'-四羟基-1,1':4',1''-三联苯-2',3'-二基二(苯乙酸酯)
  参考文献：
  名称：

  First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

  摘要：

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.

  DOI：

  10.1021/ol701590b
• 作为产物：
  描述：

  5,6-bis(methoxymethoxy)benzo[d][1,3]dioxole 在 四(三苯基膦)钯 吡啶 、 potassium phosphate 、 正丁基锂 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 49.33h， 生成 4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole-5,6-dione
  参考文献：
  名称：

  First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

  摘要：

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.

  DOI：

  10.1021/ol701590b

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。
• Studies on Natural<i>p</i>-Terphenyls: Total Syntheses of Vialinin A and Terrestrin B
  作者：Yue Qi YE、Hiroyuki KOSHINO、Jun-ichi ONOSE、Kunie YOSHIKAWA、Naoki ABE、Shunya TAKAHASHI

  DOI：10.1271/bbb.90661

  日期：2010.1.23

  A powerful inhibitor of TNF-α production, vialinin A, was synthesized from sesamol through a series of reactions involving double Suzuki-Miyaura coupling, 2,3-dichloro-5,6-dicyano-1,4-benzoquino (DDQ) mediated de-methoxymethylation and oxidative removal of methylene acetal by lead tetraacetate. The synthetic method also made it possible to prepare a related compound, terrestrin B.

  通过一系列反应，包括双铃木-宫浦偶联、2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）介导的脱甲氧基甲基化和四乙酸铅氧化脱亚甲基乙缩醛，从芝麻酚合成了一种强效的 TNF-α 生成抑制剂--vialinin A。这种合成方法还可以制备一种相关化合物--terrestrin B。
• 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.
• First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production
  作者：Yue Qi Ye、Hiroyuki Koshino、Jun-ichi Onose、Kunie Yoshikawa、Naoki Abe、Shunya Takahashi

  DOI：10.1021/ol701590b

  日期：2007.10.1

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.