2,3,4,5-tetramethoxyphenylboronic acid | 857674-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,4,5-tetramethoxyphenylboronic acid
• 英文别名: (2,3,4,5-Tetramethoxyphenyl)boronic acid；(2,3,4,5-tetramethoxyphenyl)boronic acid
• CAS: 857674-57-8
• 化学式: C₁₀H₁₅BO₆
• 分子量: 242.036
• InChiKey: JPIGHTPMRMMZRC-UHFFFAOYSA-N

物化性质

• 沸点：
  409.6±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetramethoxyphenylboronic acid 在 tris-(dibenzylideneacetone)dipalladium(0) potassium phosphate 、 ammonium cerium(IV) nitrate 、 双(2-二苯基磷苯基)醚 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 2-(4,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)benzoic acid methyl ester
  参考文献：
  名称：

  A New Fluorogenic Transformation:  Development of an Optical Probe for Coenzyme Q

  摘要：

  [GRAPHICS]A new fluorogenic transformation based on a quinone reduction/lactonization sequence has been developed and evaluated as a tool for probing redox phenomena in a biochemical context. The probe presented herein is an irreversible redox probe and is reduced selectively by biologically relevant quinols such as ubiquinol but is inert to reduced nicotinamides (e.g., NADH). The ensuing cyclization is fast and quantitative and provides a measurable optical response.

  DOI：

  10.1021/ol0507569
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 正丁基锂 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.25h， 生成 2,3,4,5-tetramethoxyphenylboronic acid
  参考文献：
  名称：

  以新开发的7-苄氧基-3-氯-8-甲氧基-2H-色烯为前体合成3种8-甲氧基异黄烷

  摘要：

  我们描述了通过基于芳基 2,3-二氯烯丙基醚的克莱森重排和随后的脱氯化氢-环化的级联反应形成 3-氯-2 H-色烯。通过在级联反应产生的 3-氯-2 H-色烯和易于制备的芳基硼酸之间进行 Suzuki 交叉偶联，实现了三种不同 3-异黄烷衍生物的不同合成。通过以下多相催化加氢，我们还完成了异黄烷天然产物（±）-duartin、（±）-7-羟基-2'、3'、4'、5'、8-五甲氧基异黄烷和（ ±)-8-甲氧基肌醇。

  DOI：

  10.1016/j.tet.2022.132714

文献信息

• Studies toward the Development of Antiproliferative Neoclerodanes from Salvinorin A
  作者：Tamara Vasiljevik、Chad E. Groer、Kurt Lehner、Hernan Navarro、Thomas E. Prisinzano

  DOI：10.1021/np5002048

  日期：2014.8.22

  The success rate for central nervous system (CNS) drug candidates in the clinic is relatively low compared to the industry average across other therapeutic areas. Penetration through the blood-brain barrier (BBB) to reach the therapeutic target is a major obstacle in development. The rapid CNS penetration of salvinorin A has suggested that the neoderodane nucleus offers an excellent scaffold for developing antiproliferative compounds that enter the CNS. The Liebeskind-Srogl reaction was used as the main carbon-carbon bond-forming step toward the synthesis of quinone-containing salvinorin A analogues. Quinone-containing salvinorin A analogues were shown to have antiproliferative activity against the MCF7 breast cancer cell line, but show no significant activity at the x-opioid receptors. In an in vitro model of BBB penetration, quinone-containing salvinorin A analogues were shown to passively diffuse across the cell monolayer. The analogues, however, are substrates of P-glycoprotein, and thus further modification of the molecules is needed to reduce the affinity for the efflux transporter.
• Design, synthesis, and biological evaluation of the analogues of glaziovianin A, a potent antitumor isoflavone
  作者：Ichiro Hayakawa、Akiyuki Ikedo、Takumi Chinen、Takeo Usui、Hideo Kigoshi

  DOI：10.1016/j.bmc.2012.08.005

  日期：2012.10

  Various analogues of glaziovianin A, an antitumor isoflavone, were synthesized, and their biological activities were evaluated. O-7-modified glaziovianin A showed strong cytotoxicity against HeLa S-3 cells. Compared to glaziovianin A, the O-7-benzyl and O-7-propargyl analogues were more cytotoxic against HeLa S-3 cells and more potent M-phase inhibitors. Furthermore, O-7-modified molecular probes of glaziovianin A were synthesized for biological studies. (C) 2012 Elsevier Ltd. All rights reserved.
• Structure–activity relationship study of glaziovianin A against cell cycle progression and spindle formation of HeLa S3 cells
  作者：Akiyuki Ikedo、Ichiro Hayakawa、Takeo Usui、Sayaka Kazami、Hiroyuki Osada、Hideo Kigoshi

  DOI：10.1016/j.bmcl.2010.07.111

  日期：2010.9

  Various derivatives of glaziovianin A, an antitumor isoflavone, were synthesized, and the cytotoxicity of each against HeLa S-3 cells was investigated. Compared to glaziovianin A, the O-7-allyl derivative was found to be more cytotoxic against HeLa S-3 cells and a more potent M-phase inhibitor. (c) 2010 Elsevier Ltd. All rights reserved.
• A New Fluorogenic Transformation:  Development of an Optical Probe for Coenzyme Q
  作者：Matthew S. Tremblay、Dalibor Sames

  DOI：10.1021/ol0507569

  日期：2005.6.1

  [GRAPHICS]A new fluorogenic transformation based on a quinone reduction/lactonization sequence has been developed and evaluated as a tool for probing redox phenomena in a biochemical context. The probe presented herein is an irreversible redox probe and is reduced selectively by biologically relevant quinols such as ubiquinol but is inert to reduced nicotinamides (e.g., NADH). The ensuing cyclization is fast and quantitative and provides a measurable optical response.
• Syntheses of three 8-methoxyisoflavans from newly developed 7-benzyloxy-3-chloro-8-methoxy-2H-chromene as the precursor
  作者：Bubwoong Kang、Takuto Oe、Yuki Shimizu、Hirosato Takikawa

  DOI：10.1016/j.tet.2022.132714

  日期：2022.5

  We describe the formation of a 3-chloro-2H-chromene via the cascade reaction based on Claisen rearrangement of an aryl 2,3-dichloroallyl ether and the subsequent dehydrochlorination-cyclization. A divergent synthesis of three different 3-isoflavan derivatives was realized by conducting a Suzuki cross-coupling between the cascade reaction-produced 3-chloro-2H-chromene and readily preparable aryl boronic

  我们描述了通过基于芳基 2,3-二氯烯丙基醚的克莱森重排和随后的脱氯化氢-环化的级联反应形成 3-氯-2 H-色烯。通过在级联反应产生的 3-氯-2 H-色烯和易于制备的芳基硼酸之间进行 Suzuki 交叉偶联，实现了三种不同 3-异黄烷衍生物的不同合成。通过以下多相催化加氢，我们还完成了异黄烷天然产物（±）-duartin、（±）-7-羟基-2'、3'、4'、5'、8-五甲氧基异黄烷和（ ±)-8-甲氧基肌醇。