2-氯-3-[2-(二甲氨基)乙胺基]萘-1,4-二酮 | 83027-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-3-[2-(二甲氨基)乙胺基]萘-1,4-二酮
• 英文名称: 2-chloro-3-(2-(dimethylamino)ethylamino)-1,4-naphthoquinone
• 英文别名: 2-Chloro-3-(2-dimethylaminoethylamino)naphthalene-1,4-dione；2-chloro-3-[2-(dimethylamino)ethylamino]naphthalene-1,4-dione
• CAS: 83027-27-4
• 化学式: C₁₄H₁₅ClN₂O₂
• 分子量: 278.738
• InChiKey: ZEYYTNKEDFUTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-3-[2-(二甲氨基)乙胺基]萘-1,4-二酮 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  pH-Dependent Rectification in Redox Polymers:  Characterization of Electrode-Confined Siloxane Polymers Containing Naphthoquinone and Benzylviologen Subunits

  摘要：

  This paper describes the electrochemical characterization of electrode-confined siloxane polymers that contain both naphthoquinone (NQ) and benzylviologen (BV2+) subunits. These ''homopolymers,'' abbreviated (NQ-BV3+)(n) and (NQ-BV-BV5+)(n), are derived from monomers, 2-chloro-3-[[2-{dimethyl[[[[N'-[[4-(trimethoxysilyl)- phenyl]methyl]-4,4'-bipyridiniumyl]methyl]phenyl]methyl]ammonium}ethyl]amino]-1,4-naphthoquinone, 1a, and 2-chloro-3-[[2-{dimethyl[[[[[[[[N'-[N'-[[4-(trimethoxysilyl)phenyl]methyl]-4,4'bipyridiniumyl]methyl]- phenyl]methyl]-4,4'-bipyridiniumyl]methyl]phenyl]methyl]ammonium}ethyl]amino]-1,4-naphthoquinone, 2a, respectively. Particular to these types of surface-confined homopolymers is the ability to ''trap'' charge at low pH in the form of reduced quinone. Between pH 10.0 and 7.0, (NQ-BV3+)(n) and (NQ-BV-BV5+)(n) undergo reversible 3e-/2H(+) and 4e-/2H(+) reduction, respectively, consistent with 2e-/2H(+) reduction of NQ subunits to the hydroquinone NQH(2) and 1e- reduction of BV2+ subunits to the radical cation BV+.. Below pH 6, however, NQ/NQH(2) reduction becomes irreversible in both polymers, whereas BV2+/+ reduction remains reversible. Electrochemical irreversibility of NQ/NQH(2) in these polymers occurs because its electrochemistry is mediated by the BV2+/+ couple. Between pH 10.0 and 7.0, BV2+/+ can mediate both reduction and oxidation of NQ/NQH(2), whereas below pH 6, the thermodynamics are such that BV2+/+ can only mediate the reduction of NQ. This behavior is similar to that of a previously studied (benzylviologen)-benzoquinone-(benzylviologen) polymer, (BV-Q-BV6+)(n).(1) Charge in the form of reduced quinone is trapped in (BV-Q-BV6+)(n) at low pH because there is essentially no direct charge transport through the Q/QH(2) system. Charge is also trapped in high coverages of (NQ-BV3+)(n) and (NQ-BV-BV5+)(n), indicating no direct charge transport through the NQ/NQH(2) system. Unlike (BV-Q-BV6+)(n), however, monolayers comprised of 1a or 2a exhibit charge transport through the NQ/NQH(2) system. The flexibility of these monolayers apparently allows direct contact of the NQ subunit with the electrode surface. Less flexible and more robust surface-confined polymers, abbreviated (NQ-BV3+/siloxane)(n) and (NQ-BV-BV5+/siloxane)(n), can be prepared by copolymerization of 1a or 2a with 1,2-bis(trimethoxysilyl)ethane. Charge trapped in (NQH(2)-BV3+/siloxane)(n) or (NQH(2)-BV-BV5+/siloxane)(n) can be released and delivered to the surface of the electrode via chemical mediation or by an increase in solution pH. For example, the redox couple I-3(-)/I- will catalytically release the trapped charge when the potential of the electrode is brought close to E(o)'(I-3(-)/I-). Surfaces modified with (NQ-BV3+/siloxane)(n) or (NQ-BV-BV5+/siloxane)(n), however, are impermeable to the large anionic redox couple Fe(CN)(6)(3-/4-), preventing mediated charge release by this reagent.The lack of electrostatic binding of Fe(CN)(6)(3-/4-) to electrodes modified with (NQ-BV3+/siloxane)(n) or (NQ-BV-BV5+/siloxane)(n) suggests a high degree of crosslinking in these polymers provided by 1,2-bis(trimethoxysilyl)ethane. At neutral pH, dioxygen will chemically induce the release of charge trapped in (NQH(2)-BV3+/siloxane)(n) or (NQH(2)-BV-BV5+/siloxane)(n). The irreversible production of H2O2 upon oxidation of NQH(2) in water, however, prevents the return of charge to the electrode. Charge release is also demonstrated by pH jump experiments where an increase in pH shifts E(o)'(NQ/NQH(2)) to a potential where BV2+/+ mediate the oxidation of NQH(2) to NQ and deliver charge to the electrode.

  DOI：

  10.1021/jp9626475
• 作为产物：
  描述：

  在 paraquat dichloride 、 异丙醇 作用下， 以 水 为溶剂， 生成 2-氯-3-[2-(二甲氨基)乙胺基]萘-1,4-二酮
  参考文献：
  名称：

  连接的紫精醌分子中的电子转移：速率常数随链长的增加而增强

  摘要：

  We synthesized a homologous series of molecules (MVnnQ) where a methylviologen (MV) and a aminochloronaphthoquinone (Q) are linked to each other via a flexible chain. Using the electron pulse radiolysis technique, we have measured time-resolved spectra and rate constant for intra- and intermolecular electron transfer between donor and acceptor site of the MVnnQ molecules in water and in SDS micellar solution. For comparison, we also irradiated a solution containing a 1:1 mixture of methylviologen and aminochloronaphthoquinone and measured spectra and intermolecular ET reactions between the separated electron donor and acceptor molecules. The intramolecular electron transfer rate constants of all MVnnQ molecules were surprisingly low both in water and in aqueous SDS micellar suspension. The intramolecular rate constants measured in water increase with increasing number of intervening bonds, leading to the conclusion that electron transfer occurs by a through-space rather than through-bond mechanism. The intramolecular rate constants virtually lose their chain length dependence in SDS suspensions where because of an extended configuration of the micellized MVnnQ molecules through-space interaction is not favored.

  DOI：

  10.1021/j100181a036

文献信息

• 미세조류 파괴용 조성물
  申请人：Industry-Academic Cooperation Foundation, Chosun University 조선대학교산학협력단(220050171903) BRN ▼408-82-13419

  公开号：KR101761848B1

  公开（公告）日：2017-07-26

  본 발명은 미세조류 파괴용 조성물에 관한 것으로, 더욱 자세하게는 특정 치환기를 가지는 나프토퀴논 화합물을 함유하는 미세조류 파괴용 조성물에 관한 것이다. 본 발명에 따른 신규한 미세조류 파괴용 조성물은 해양 미세조류 배양장 또는 녹조 또는 적조가 발생된 지역 또는 녹조나 적조 발생 예상 지역에 처리하여 녹조 및 적조 피해를 예방할 수 있는 효과가 있다.

  本发明涉及微藻破坏用配方，更具体地涉及含有特定取代基的萘酮化合物的微藻破坏用配方。根据本发明，新型微藻破坏用配方可在海洋微藻培养场或发生褐藻或红藻的区域或预计发生褐藻或红藻的区域进行处理，以预防褐藻和红藻的损害。
• Dioxonaphthoimidazoliums are Potent and Selective Rogue Stem Cell Clearing Agents with SOX2-Suppressing Properties
  作者：Si-Han Sherman Ho、Azhar Ali、Yi-Cheng Ng、Kuen-Kuen Millie Lam、Shu Wang、Woon-Khiong Chan、Tan-Min Chin、Mei-Lin Go

  DOI：10.1002/cmdc.201600262

  日期：2016.9.6

  non‐pharmacological methods. Dioxonapthoimidazolium YM155, a survivin suppressant, induced selective and potent cell death of undifferentiated stem cells. Herein, the structural requirements for stemotoxicity were investigated and found to be closely aligned with those essential for cytotoxicity in malignant cells. There was a critical reliance on the quinone and imidazolium moieties but a lesser dependence on

  多能干细胞在再生医学方面具有独特的定位，但只有将其致瘤倾向与其多能特性脱钩，才能实现其临床潜力。使用小分子去除残留的未分化多能细胞，否则这些细胞会转化为畸胎瘤和畸胎瘤，与非药物方法相比具有几个优势。Dioxonapthoimidazolium YM155 是一种存活素抑制剂，可诱导未分化干细胞的选择性和强效细胞死亡。在此，对干细胞毒性的结构要求进行了研究，发现其与恶性细胞中细胞毒性所必需的结构要求密切相关。对醌和咪唑鎓部分的依赖性很大，但对环取代基的依赖性较小，主要用于微调活动。鉴定出几种有效的类似物，如 YM155，抑制干细胞中的 survivin 并降低 SOX2。SOX2 的减少会导致多能因子的不平衡，这可能会促使细胞分化，从而降低异常畸胎瘤形成的风险。由于 NF-κB p50 亚基的磷酸化也被抑制，磷酸化-p50、SOX2 和 survivin 之间的串扰可能暗示 NF-κB 信号
• Mediated electrochemical reduction of oxygen to hydrogen peroxide via a surface-confined naphthoquinone reagent and the mediated electrochemical reduction of a naphthoquinone redox reagent anchored to high surface area oxides
  作者：Gary S. Calabrese、Robert M. Buchanan、Mark S. Wrighton

  DOI：10.1021/ja00355a011

  日期：1983.8

  approx. 0.8 V more positive than at a metallic electode. The overall energetics are such that light can be used to effect the uphill formation of H/sub 2/O/sub 2/ via the quinone-mediated reduction of O/sub 2/. The onset of O/sub 2/ reduction is up to 0.6 V more positive than E/sup 0/'(O/sub 2//H/sub 2/O/sub 2/). The sustained photoassisted reduction of O/sub 2/ to H/sub 2/O/sub 2/ has been demonstrated

  1,4-萘醌、2-氯-3-((2-(二甲基丙基氨)乙基)氨基)-1,4-萘醌溴化物、Ia和2-氯-3-((2-(二甲基(3 -(三甲氧基甲硅烷基)丙基)氨基)乙基)氨基)-1,4-萘醌溴化物，Ib，已被合成并用作溶液和表面结合催化剂，分别用于O/sub 2/的电化学和光电化学还原H/sub 2/O/sub 2/。具有-Si(OCH/sub 3/)/sub 3/ 官能度的表面衍生试剂Ib可用于官能化多种表面，包括电极材料和高表面积氧化物。表面试剂 (Q/QH/sub 2/)/sub surf/ 与溶液中的 Ia 具有相同的 E/sup 0/'，大约为 -0.4 V vs. pH 7 时的 SCE。 (QH/sub 2/)/sub surf/ 在 pH 7 的水性电解质中与 O/sub 2/ 反应，速率常数 > 10/sup 5/ M/sup -1/s/sup -1/形成H/sub 2/O/sub
• Electrochemical behavior of a surface-confined naphthoquinone derivative.Electrochemical and photoelectrochemical reduction of oxygen to hydrogen peroxide at derivatized electrodes
  作者：Gary S. Calabrese、Robert M. Buchanan、Mark S. Wrighton

  DOI：10.1021/ja00385a040

  日期：1982.10
• US4576756A
  申请人：——

  公开号：US4576756A

  公开（公告）日：1986-03-18