2-氯-5-羟基-1,4-苯醌 | 89284-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-5-羟基-1,4-苯醌
• 英文名称: 2,5-Cyclohexadiene-1,4-dione, 2-chloro-5-hydroxy-
• 英文别名: 2-chloro-5-hydroxy-1,4-benzoquinone；5-chloro-2-hydroxy-p-benzoquinone；5-chloro-2-hydroxybenzoquinone；2-chloro-5-hydroxy-[1,4]benzoquinone；2-Chlor-5-hydroxy-[1,4]benzochinon；2-Chlor-5-hydroxy-chinon
• CAS: 89284-69-5
• 化学式: C₆H₃ClO₃
• 分子量: 158.541
• InChiKey: QDGSLISDGXAGPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-氯-5-羟基-1,4-苯醌 在 还原型辅酶Ⅰ 作用下， 生成 5-氯-4-羟基邻苯二酚
  参考文献：
  名称：

  Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

  摘要：

  Burkholderia cepacia AC1100 completely degrades 2,4,5-trichlorophenol, in which an FADH(2)-dependent monooxygenase (TftD) and an NADH: FAD oxidoreductase (TftC) catalyze the initial steps. TftD oxidizes 2,4,5-trichlorophenol (2,4,5-TCP) to 2,5-dichloro-p-benzoquinone, which is chemically reduced to 2,5-dichloro-p-hydroquinone (2,5-DiCHQ). Then, TftD oxidizes the latter to 5-chloro-2-hydroxy-p-benzoquinone. In those processes, TftC provides all the required FADH(2). We have determined the crystal structures of dimeric TftC and tetrameric TftD at 2.0 and 2.5 angstrom resolution, respectively. The structure of TftC was similar to those of related flavin reductases. The stacked nicotinamide: isoalloxazine rings in TftC and sequential reaction kinetics suggest that the reduced FAD leaves TftC after NADH oxidation. The structure of TftD was also similar to the known structures of FADH(2)-dependent monooxygenases. Its His-289 residue in the re-side of the isoalloxazine ring is within hydrogen bonding distance with a hydroxyl group of 2,5-DiCHQ. An H289 A mutation resulted in the complete loss of activity toward 2,5-DiCHQ and a significant decrease in catalytic efficiency toward 2,4,5-TCP. Thus, His-289 plays different roles in the catalysis of 2,4,5-TCP and 2,5-DiCHQ. The results support that free FADH(2) is generated by TftC, and TftD uses FADH(2) to separately transform 2,4,5-TCP and 2,5-DiCHQ. Additional experimental data also support the diffusion of FADH(2) between TftC and TftD without direct physical interaction between the two enzymes.

  DOI：

  10.1074/jbc.m109.056135
• 作为产物：
  描述：

  2,5-二氯对苯二酚 在 [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[[(2R,3S,4S)-5-(7,8-二甲基-2,4-二氧代-1,5-二氢苯并[g]蝶啶-10-基)-2,3,4-三羟基戊氧基]-羟基磷酰]磷酸氢酯 、 chlorophenol 4-monooxygenase of Burkholderia cepacia AC₁₁₀₀ 、 NADH:FAD oxidoreductase of Burkholderia cepacia AC₁₁₀₀ 作用下， 生成 2-氯-5-羟基-1,4-苯醌
  参考文献：
  名称：

  Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

  摘要：

  Burkholderia cepacia AC1100 completely degrades 2,4,5-trichlorophenol, in which an FADH(2)-dependent monooxygenase (TftD) and an NADH: FAD oxidoreductase (TftC) catalyze the initial steps. TftD oxidizes 2,4,5-trichlorophenol (2,4,5-TCP) to 2,5-dichloro-p-benzoquinone, which is chemically reduced to 2,5-dichloro-p-hydroquinone (2,5-DiCHQ). Then, TftD oxidizes the latter to 5-chloro-2-hydroxy-p-benzoquinone. In those processes, TftC provides all the required FADH(2). We have determined the crystal structures of dimeric TftC and tetrameric TftD at 2.0 and 2.5 angstrom resolution, respectively. The structure of TftC was similar to those of related flavin reductases. The stacked nicotinamide: isoalloxazine rings in TftC and sequential reaction kinetics suggest that the reduced FAD leaves TftC after NADH oxidation. The structure of TftD was also similar to the known structures of FADH(2)-dependent monooxygenases. Its His-289 residue in the re-side of the isoalloxazine ring is within hydrogen bonding distance with a hydroxyl group of 2,5-DiCHQ. An H289 A mutation resulted in the complete loss of activity toward 2,5-DiCHQ and a significant decrease in catalytic efficiency toward 2,4,5-TCP. Thus, His-289 plays different roles in the catalysis of 2,4,5-TCP and 2,5-DiCHQ. The results support that free FADH(2) is generated by TftC, and TftD uses FADH(2) to separately transform 2,4,5-TCP and 2,5-DiCHQ. Additional experimental data also support the diffusion of FADH(2) between TftC and TftD without direct physical interaction between the two enzymes.

  DOI：

  10.1074/jbc.m109.056135

文献信息

• A Combined Experimental and Computational Investigation on the Unusual Molecular Mechanism of the Lossen Rearrangement Reaction Activated by Carcinogenic Halogenated Quinones
  作者：Guo-Qiang Shan、Ao Yu、Chuan-Fang Zhao、Chun-Hua Huang、Ling-Yan Zhu、Ben-Zhan Zhu

  DOI：10.1021/jo5022713

  日期：2015.1.2

  describing the transformation of an O-activated hydroxamic acid into the corresponding isocyanate. In this study, we found that chlorinated benzoquinones (CnBQ) serve as a new class of agents for the activation of benzohydroxamic acid (BHA), leading to Lossen rearrangement. Compared to the classic one, this new kind of CnBQ-activated Lossen rearrangement has the following unique characteristics: (1) The

  经典的洛森重​​排是一种众所周知的反应，描述了O活化的异羟肟酸向相应异氰酸酯的转化。在这项研究中，我们发现氯代苯醌（C n BQ）作为一类新的苯并异羟肟酸（BHA）活化剂，导致Lossen重排。与经典的相比，这种新型的C n BQ活化的Lossen重排具有以下独特特征：（1）发现C n BQ活化的BHA中间体的稳定性不仅取决于程度，而且取决于位置C n BQs上Cl取代的关系，可以分为两个子组。（2）是阴离子C n的相对能量确定此C n BQ活化重排速率的BQ–BHA中间体是限速步骤，而C n BQ邻位至反应位点的Cl或H对于阴离子中间体的稳定性至关重要。（3）的p ķ一个观察-activation能量相关性，这可以解释为什么重排的速率和阴离子离去基团，所述hydroxlated醌的共轭酸的酸度之间存在的相关性。这些发现可能对卤代醌类致癌物和异羟肟酸酯生物医学药物的未来研究具有广泛的意义。
• Compositions for repelling crawling insects
  申请人：——

  公开号：US20020094993A1

  公开（公告）日：2002-07-18

  The present invention relates to novel compositions, comprising a repellent and an additive, where the additive is selected from the group consisting of phenol, benzaldehyde, benzoic acid or derivatives thereof and is present in a ratio of from 10:100 to 200:100% by weight to the repellent, and to their use for repelling crawling harmful insects, in particular ants or cockroaches.

  本发明涉及新型组合物，包括一种驱虫剂和一种添加剂，其中所述添加剂选自苯酚、苯甲醛、苯甲酸或其衍生物组成的群体，并以10:100至200:100％重量的比例存在于驱虫剂中，以及其用于驱赶爬行有害昆虫，特别是蚂蚁或蟑螂。
• Stieglitz, American Chemical Journal, 1891, vol. 13, p. 38
  作者：Stieglitz

  DOI：——

  日期：——
• Photocatalytic Degradation of 4-Chlorophenol. 2. The 4-Chlorocatechol Pathway
  作者：Xiaojing Li、Jerry W. Cubbage、William S. Jenks

  DOI：10.1021/jo990912n

  日期：1999.11.1

  The TiO2-mediated photocatalytic degradation of 4-chlorocatechol is studied as a branch of the degradation of 4-chlorophenol. In addition to some basic kinetic studies, the identities of many of the cyclic and acyclic intermediates, verified in most cases with authentic samples, are reported. From 4-chlorocatechol, the major product is hydroxylation to form 5-chloro-1,2,4-benzenetriol. A small amount of 4-chloropyrogallol is also produced. Substitution to give 1,2,4-benzenetriol is observed as is oxidative cleavage of the C1-C2 bond to give the diacid. The major products of all of the triols are those of oxidative cleavages, occurring mainly between ortho hydroxy-substituted carbons to give diacids but also between one hydroxy and one unsubstituted carbon to give acid-aldehydes. Many smaller intermediates in the degradations are identified, and pathways are proposed for the larger compounds.
• ZUSAMMENSETZUNGEN ZUR ABSCHRECKUNG KRIECHENDER INSEKTEN
  申请人：Bayer Aktiengesellschaft

  公开号：EP1304924A2

  公开（公告）日：2003-05-02