2,3-dichloro-6-hydroxy-1,4-naphthoquinone | 127042-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dichloro-6-hydroxy-1,4-naphthoquinone
• 英文别名: 2,3-dichloro-6-hydroxynaphthoquinone；2,3-Dichloro-6-hydroxynaphthalene-1,4-dione；2,3-dichloro-6-hydroxynaphthalene-1,4-dione
• CAS: 127042-42-6
• 化学式: C₁₀H₄Cl₂O₃
• 分子量: 243.046
• InChiKey: LBVTYPQMSCIDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 2,3-dichloro-6-hydroxy-1,4-naphthoquinone 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 以56%的产率得到2,3-dichloro-6-n-pentyloxy-1,4-naphthoquinone
  参考文献：
  名称：

  Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone

  摘要：

  Conocurvone 是一种从澳大利亚特有灌木 Conosperum sp.（原生植物科）中分离出来的新型天然产物，具有抗艾滋病毒的活性，但它是一种高亲脂性化合物，这表明它的水溶性和生物利用度可能存在问题。本文介绍了一种利用 2-羟基萘醌和 2,3-二卤醌缩合合成三聚萘醌的通用简便方法。报告还介绍了应用这种方法合成一系列更简单、亲油性更低的三聚萘醌简单类似物 conocurvone 及其抗 HIV 活性。

  DOI：

  10.1071/ch08177
• 作为产物：
  描述：

  (4aR,8S,8aS)-2,3,4a,8a-Tetrachloro-8-methoxy-4a,7,8,8a-tetrahydro-5H-naphthalene-1,4,6-trione 在 锌 作用下， 以43%的产率得到2,3-dichloro-6-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Dichloro quinones as dienophiles: synthesis of alizarin derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(01)93478-1

文献信息

• Antiviral agents 2. Synthesis of trimeric naphthoquinone analogues of conocurvone and their antiviral evaluation against HIV
  作者：Ian T. Crosby、David G. Bourke、Eric D. Jones、Paula J. de Bruyn、David Rhodes、Nick Vandegraaff、Susan Cox、Jonathan A.V. Coates、Alan D. Robertson

  DOI：10.1016/j.bmc.2010.06.105

  日期：2010.9

  The synthesis of a new series of conocurvone analogues is presented that explores the importance of the pyran rings of conocurvone, their degree of unsaturation as well as the role of alkoxy functionalities as pyran ring replacements, for the inhibition of the HIV-1 integrase (IN) enzyme. Difficulties in synthesising a trimeric naphthoquinone where the central quinone bears a peri-dihydropyran ring was attributed to distortion of the electrophilic dihaloquinone successfully utilised in the past. Increased electron density could also be a factor in reducing reactivity. The desired central dihydropyran bearing trimeric naphthoquinone was successfully synthesised by using a more reactive bromo-tosyloxyquinone intermediate. A maleimide derivative, where the central quinone between the pendant hydroxyquinones was replaced, was successfully synthesised and although it exhibited comparable enzyme inhibitory activity it had negligible HIV inhibitory cellular activity. Compounds were assessed for activity in both in vitro assays using purified recombinant HIV-1 IN and demonstrated superior or comparable activity to conocurvone derivatives previously reported. (C) 2010 Elsevier Ltd. All rights reserved.
• RADICAL POLYMERIZATION CONTROL AGENT AND RADICAL POLYMERIZATION CONTROL METHOD
  申请人：Kawasaki Kasei Chemicals Ltd.

  公开号：US20210122692A1

  公开（公告）日：2021-04-29

  A conventional polymerization inhibitor is for example an agent to scavenge radicals generated during storage of a radical polymerizable compound and used to stably handle the radical polymerizable compound, but is unnecessary when the radical polymerizable compound is to be subjected to radical polymerization reaction, and is preferably removed at the time of the radical polymerization reaction. The object of the present invention is to obviate inconvenience of removing the polymerization inhibitor at the time of radical polymerization. The radical polymerization control agent contained in a radical polymerizable composition of the present invention functions as a radical polymerization inhibitor for example stored in a dark place, but loses its radical polymerization inhibiting effect when polymerization is initiated while being irradiated with light at a certain specific wavelength at the time of polymerization. Thus, radical polymerization of the radical polymerizable compound is easily initiated without increasing the amount of a radical polymerization initiator. That is, the radical polymerization control agent of the present invention is a radical polymerization control agent which is a corn pound having an effect to inhibit radical polymerization of a radical polymerizable compound and which loses the radical polymerization inhibiting effect under irradiation with light rays containing light within a wavelength range of from 300 nm to 500 nm.
• Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone
  作者：Ian T. Crosby、Mark L. Rose、Maree P. Collis、Paula J. de Bruyn、Philip L. C. Keep、Alan D. Robertson

  DOI：10.1071/ch08177

  日期：——

  Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity.

  Conocurvone 是一种从澳大利亚特有灌木 Conosperum sp.（原生植物科）中分离出来的新型天然产物，具有抗艾滋病毒的活性，但它是一种高亲脂性化合物，这表明它的水溶性和生物利用度可能存在问题。本文介绍了一种利用 2-羟基萘醌和 2,3-二卤醌缩合合成三聚萘醌的通用简便方法。报告还介绍了应用这种方法合成一系列更简单、亲油性更低的三聚萘醌简单类似物 conocurvone 及其抗 HIV 活性。
• Dichloro quinones as dienophiles: synthesis of alizarin derivatives
  作者：Donald W. Cameron、Geoffrey I. Feutrill、Philip L.C. Keep

  DOI：10.1016/s0040-4039(01)93478-1

  日期：——