4-methoxy-3-(methoxymethoxy)phenylboronic acid | 1225441-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-3-(methoxymethoxy)phenylboronic acid
• 英文别名: [4-Methoxy-3-(methoxymethoxy)phenyl]boronic acid
• CAS: 1225441-53-1
• 化学式: C₉H₁₃BO₅
• 分子量: 212.01
• InChiKey: PFUWVWOUNDYJDP-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-(methoxymethoxy)phenylboronic acid 在 盐酸 、 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四丁基溴化铵 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 3.5h， 生成 4-(3'-hydroxy-4'-methoxyphenyl)-5-methoxycoumarin
  参考文献：
  名称：

  Synthesis of hydrophilic and lipophilic 4-arylcoumarin phosphates

  摘要：

  新型亲水性和疏水性前药，四芳基香豆烯二烷基磷酸盐和四芳基香豆烯二油酸磷酸盐，是通过将四芳基香豆烯与二烷基磷酸酯磷酸化合成的。

  DOI：

  10.1007/s11172-011-0304-7
• 作为产物：
  描述：

  4-bromo-1-methoxy-2-(methoxymethoxy)benzene 在 叔丁基锂 、 硼酸三甲酯 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-methoxy-3-(methoxymethoxy)phenylboronic acid
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

  摘要：

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.030

文献信息

• Hypervalent‐Iodine(III)‐Mediated Tandem Oxidative Dearomatization/Aziridination of Phenolic Amines: Synthesis of Functionalized Unactivated Aziridines
  作者：Ye‐Xing Cao、Patamawadee Silalai、Chun‐Fang Liu、Ke‐Yin Yu、Xu Bao、Xian‐He Zhao、Rungnapha Saeeng、Chun‐An Fan

  DOI：10.1002/chem.202100762

  日期：2021.6.10

  A new hypervalent-iodine(III)-mediated tandem reaction involving oxidative dearomatization and in situ aziridination of phenolic amines is described, providing a mild and effective method for the assembly of structurally interesting and synthetically useful aziridines. Importantly, the densely functionalized aziridines resulting from this unprecedented tandem reaction offer a platform for expeditious

  描述了一种新的高价碘 (III) 介导的串联反应，涉及酚胺的氧化脱芳构化和原位氮丙啶化，为组装结构有趣且合成有用的氮丙啶提供了一种温和而有效的方法。重要的是，这种前所未有的串联反应产生的密集功能化的氮丙啶提供了一个平台，通过氮丙啶的选择性开环引发的转化，可以快速获得结构多样的氮杂杂环。
• Divergent Synthesis of Lamellarin α 13-Sulfate, 20-Sulfate, and 13,20-Disulfate
  作者：Masatomo Iwao、Tsutomu Fukuda、Sho Saeki、Takeshi Ohta

  DOI：10.3987/com-09-s(s)100

  日期：——

  A divergent synthesis of three sulfate derivatives of lamellarin alpha, namely, lamellarin alpha 13-sulfate (2), 20-sulfate (1), and 13,20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the lamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3,4-dihydroxypyrrole bistriflate (7) as a key reaction.
• Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues
  作者：Haruka Kamiyama、Yoshinao Kubo、Hironori Sato、Naoki Yamamoto、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.bmc.2011.10.030

  日期：2011.12

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of hydrophilic and lipophilic 4-arylcoumarin phosphates
  作者：A. N. Selikhov、Y. B. Malysheva、A. V. Nyuchev、N. S. Sitnikov、E. A. Sharonova、A. S. Shavyrin、S. Combes、A. Yu. Fedorov

  DOI：10.1007/s11172-011-0304-7

  日期：2011.10

  Novel hydrophilic and lipophilic prodrugs, sodium 4-arylcoumarin dialkylphosphates and 4-arylcoumarin dioleyl phosphates, were synthesized by phosphorylation of 4-arylcoumarins with dialkylphosphites.

  新型亲水性和疏水性前药，四芳基香豆烯二烷基磷酸盐和四芳基香豆烯二油酸磷酸盐，是通过将四芳基香豆烯与二烷基磷酸酯磷酸化合成的。