4-chlorocyclohexa-3,5-diene-1,2-dione | 31222-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chlorocyclohexa-3,5-diene-1,2-dione
• 英文别名: 4-chloro-1,2-benzoquinone；4-chloro-o-benzoquinone；4-chloro-o-quinone；4-chloro-[1,2]benzoquinone；4-Chlor-[1,2]benzochinon；4-Chlor-o-chinon
• CAS: 31222-02-3
• 化学式: C₆H₃ClO₂
• mdl: MFCD01663140
• 分子量: 142.542
• InChiKey: LOLOOGVNFWMAIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chlorocyclohexa-3,5-diene-1,2-dione 生成 4-氯邻苯二酚
  参考文献：
  名称：

  Enzymically Amplified Voltammetric Sensor for Microliter Sample Volumes of Salicylate

  摘要：

  A new voltammetric sensing strategy for salicylate employing two enzymes and applicable to microliter sample volumes is demonstrated, The method involves the use of the enzyme salicylate hydroxylase to convert salicylate to catechol, which is oxidized at a carbon electrode, The product of this oxidation reaction, o-quinone, is then reduced by a second enzyme, glucose oxidase, to regenerate catechol, Reoxidation of catechol results in a signal that is amplified due to repeated cycling of catechol molecules between the oxidized and reduced states, This chemistry is implemented in two configurations, (i) A paper disk into which both enzymes have been absorbed is mounted on a coplanar three electrode assembly for aqueous experiments, Determination of salicylate in a nonprescription dermatological product is demonstrated, (ii) A small solution volume confined directly on the coplanar electrodes is used for determination of salicylate in whole blood, The advantages of the use of two enzymes and of monitoring steady-state catalytic currents are discussed.

  DOI：

  10.1021/ac00107a022
• 作为产物：
  描述：

  2-苯醌 在 盐酸 、 乙醚 、 sodium sulfate 、 silver(l) oxide 作用下， 生成 4-chlorocyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  Willstaetter; Mueller, Chemische Berichte, 1911, vol. 44, p. 2179

  摘要：

  DOI：

文献信息

• METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
  申请人：THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY

  公开号：US20170066711A1

  公开（公告）日：2017-03-09

  A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:

  提供一种从含有所述芳香C—O键的羟基芳烃制备具有芳香C—N键正交于芳香C—O键的芳烃的方法。该方法包括以下步骤：a) 对羟基芳烃进行正交氧化以产生一个正交醌，b) 将正交醌与氮亲核试剂缩合以生成化合物IVa或IVb的化合物，c) 允许化合物IVa或IVb发生1,5-氢原子转移，从而分别产生具有化合物Va和Vb的C—O键正交的C—N键的芳烃。
• Dearomatization of Electron‐Deficient Phenols to <i>ortho</i> ‐Quinones: Bidentate Nitrogen‐Ligated Iodine(V) Reagents
  作者：Xiao Xiao、Nathaniel S. Greenwood、Sarah E. Wengryniuk

  DOI：10.1002/anie.201909868

  日期：2019.11.4

  ortho‐quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen‐ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)‐HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho‐quinone products was examined, resulting in a facile one‐pot synthesis

  尽管其用途广泛，邻醌的合成仍然是一个重大挑战，特别是获得缺电子衍生物仍然是一个未解决的问题。这里报道了第一个通过酚类直接氧化合成缺电子邻醌的通用方法。该反应是通过一种新型双齿氮连接碘 (V) 试剂实现的，这是一类以前未开发的化合物，我们将其称为 Bi( N )-HVI。该反应非常普遍，并且对于邻位异构体和对位异构体具有优异的区域选择性。对邻醌产物的官能化进行了检查，从而实现了儿茶酚的简单一锅合成，以及多种杂原子亲核试剂的掺入。该方法代表了 Bi( N )-HVI的首次合成应用，并展示了它们作为进一步开发高反应性、高度可调的 I(V) 试剂的平台的潜力。
• Associative chemosensing by fluorescent macrocycle–dye complexes – a versatile enzyme assay platform beyond indicator displacement
  作者：Frank Biedermann、Denisa Hathazi、Werner M. Nau

  DOI：10.1039/c4cc10227d

  日期：——

  Enzymatic reactions of aromatic substrates can be monitored by fluorescence with μM sensitivity in real time by using self-assembled fluorescent receptors.

  芳香底物的酶反应可以通过使用自组装荧光受体实时监测，具有微米级灵敏度的荧光。
• Reactions of some conjugated dienes with an o-quinone monoimide
  作者：Harold W. Heine、Wayne C. Schairer、Joseph A. Suriano、Elizabeth A. Williams

  DOI：10.1016/s0040-4020(01)85949-4

  日期：1988.1

  The reactions of N-(2,4-dichloro-6-oxo-2,4-cyclohexadien-1-ylidene)-4-nitrobenzamide () with various conjugated dienes have been studied. The heterodiene system of reacts with one of the double bonds of E-1, 3-pentadiene, E,E-2,4-hexadiene, E,E-1,4-diphenyl-1,3-butadiene, E,E-2,4-hexadienal, ethyl sorbate, 1-methoxy-1,3-butadiene, cyclopentadiene, 1,2,3,4-tetra-phenylcyclopentadiene in an inverse electron-demand

  研究了N-（2,4-二氯-6-氧代-2,4-环己二-1-基）-4-硝基苯甲酰胺（）与各种共轭二烯的反应。的杂二烯体系与E-1、3-戊二烯，E，E-2,4-己二烯，E，E-1,4-二苯基-1,3-丁二烯，E，E-的双键之一反应2,4-己二醛，山梨酸乙酯，1-甲氧基-1,3-丁二烯，环戊二烯，1,2,3,4-四苯基环戊二烯在反电子需求的Diels-Alder反应中生成2,3-衍生物二氢-1,4-苯并恶嗪。与上述二烯相反，在N-酰基酰亚胺基团上加成1，3-丁二烯，得到螺环加合物。
• Studies of the competing rates of catechol oxidation and suicide inactivation of tyrosinase
  作者：Christopher A. Ramsden、Patrick A. Riley

  DOI：10.3998/ark.5550190.0011.a20

  日期：——

  Tyrosinase oxidation of catechols to ortho-quinones is accompanied by suicide inactivation of the enzyme. The rates of these competing processes vary and depend on the nature of ring substituents. For a series of 4-substituted catechols the relationships between structure and reaction rates have been examined using multiple regression. Significant but different structurerate relationships were found

  酪氨酸酶将儿茶酚类氧化成邻苯醌伴随着该酶的自杀失活。这些竞争过程的速率各不相同，取决​​于环取代基的性质。对于一系列 4 取代的儿茶酚，结构和反应速率之间的关系已经使用多元回归进行了检查。每个过程都发现了显着但不同的结构速率关系。短疏水取代基的氧化速率 (k1) 最大；对于失活率 (k2)，存在最佳取代基疏水性 (π ~ 0.7)。