balsaquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: balsaquinone
• 英文别名: 2-Methoxy-3-(2-hydroxyethyl)-1,4-naphthoquinone；2-(2-hydroxyethyl)-3-methoxynaphthalene-1,4-dione
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: HVFFTDDDEQDGLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  balsaquinone 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 以7 mg的产率得到sodium 2-hydroxide-3-(2-hydroxyethyl)naphthalene-1,4-dione
  参考文献：
  名称：

  Cyclooxygenase-2 Inhibitory 1,4-Naphthoquinones from Impatiens balsamina L.

  摘要：

  在两种新的 1,4-萘醌钠盐（3-羟基-2{[3-羟基-1,4-二氧代（2-萘基）]乙基钠}萘-1、4-二酮（imatienolate）钠盐（1）和 2-羟基-3-（2-羟乙基）萘-1,4-二酮（balsaminolate）钠盐（2），它们是从 Impatiens balsamina L.（凤仙花科植物）的花冠中分离出来的。(凤仙花科）的花冠中分离出来。通过光谱技术阐明了它们的结构。我们的研究结果为使用 I. balsamina L. 治疗关节风湿、疼痛和肿胀提供了证据。

  DOI：

  10.1248/bpb.25.658
• 作为产物：
  描述：

  2-氯-3-(2-羟基乙基)-1,4-萘醌 、 氢氧化钾 、 甲醇 生成 balsaquinone
  参考文献：
  名称：

  GUPTA, R. B.;FRANCK, R. W., SYNLETT.,(1990) N, C. 355-357

  摘要：

  DOI：

文献信息

• Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone
  作者：Tokutaro Ogata、Misae Doe、Aya Matsubara、Eri Torii、Chiaki Nishiura、Arisa Nishiuchi、Yusuke Kobayashi、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2013.11.025

  日期：2014.1

  The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield. (C) 2013 Elsevier Ltd. All rights reserved.
• Cyclooxygenase-2 Inhibitory 1,4-Naphthoquinones from Impatiens balsamina L.
  作者：Hisae Oku、Kyoko Ishiguro

  DOI：10.1248/bpb.25.658

  日期：——

  Significant selective cyclooxygenase-2 (COX-2) inhibitory activities were observed for two new 1,4-naphthoquinone sodium salts, sodium 3-hydroxide-2[sodium 3-hydroxide-1,4-dioxo(2-naphthyl)]ethyl}naphthalene-1,4-dione (impatienolate) (1) and sodium 2-hydroxide-3-(2-hydroxyethyl)naphthalene-1,4-dione (balsaminolate) (2), which were isolated from the corolla of Impatiens balsamina L. (Balsaminaceae). Their structures were elucidated by spectral techniques. Our results offer evidence supporting the use of I. balsamina L. to treat articular rheumatism, pain, and swelling.

  在两种新的 1,4-萘醌钠盐（3-羟基-2[3-羟基-1,4-二氧代（2-萘基）]乙基钠}萘-1、4-二酮（imatienolate）钠盐（1）和 2-羟基-3-（2-羟乙基）萘-1,4-二酮（balsaminolate）钠盐（2），它们是从 Impatiens balsamina L.（凤仙花科植物）的花冠中分离出来的。(凤仙花科）的花冠中分离出来。通过光谱技术阐明了它们的结构。我们的研究结果为使用 I. balsamina L. 治疗关节风湿、疼痛和肿胀提供了证据。
• GUPTA, R. B.;FRANCK, R. W., SYNLETT.,(1990) N, C. 355-357
  作者：GUPTA, R. B.、FRANCK, R. W.

  DOI：——

  日期：——