N-乙酰基多巴胺苯醌 | 65717-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-乙酰基多巴胺苯醌
• 英文名称: N-acetyldopaminequinone
• 英文别名: N-Acetyldopamine quinone；N-[2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]acetamide
• CAS: 65717-99-9
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: WALUDRYRFZLUJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-乙酰基多巴胺苯醌 以 氘代丙酮 、 丙酮 为溶剂， 反应 1.05h， 生成 N-[2-(3,4-二羟基苯基)乙基]乙酰胺
  参考文献：
  名称：

  DOPA和多巴胺衍生物的化学反应性及其在亲核性氧化反应中的区域选择性

  摘要：

  四个儿茶酚胺，所述化学反应性ñ -乙酰基多巴胺（NADA）和它的衍生物脱氢（NAΔDA），ñ -乙酰基-3,4-二羟基-苯丙氨酸甲酯（NADOPAME）及其脱氢衍生物（NAΔDOPAME），下氧化亲核捕集和比较和对比聚合条件。尽管它们在结构上相似，但观察到乙硫醇氧化亲核捕获的反应性和区域选择性有所不同。这对仿生材料的设计和合成中这些天然结构单元及其衍生物的使用可能产生影响。

  DOI：

  10.1016/j.tet.2016.08.068
• 作为产物：
  描述：

  N-[2-(3,4-二羟基苯基)乙基]乙酰胺 在 silver(l) oxide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 N-乙酰基多巴胺苯醌
  参考文献：
  名称：

  DOPA和多巴胺衍生物的化学反应性及其在亲核性氧化反应中的区域选择性

  摘要：

  四个儿茶酚胺，所述化学反应性ñ -乙酰基多巴胺（NADA）和它的衍生物脱氢（NAΔDA），ñ -乙酰基-3,4-二羟基-苯丙氨酸甲酯（NADOPAME）及其脱氢衍生物（NAΔDOPAME），下氧化亲核捕集和比较和对比聚合条件。尽管它们在结构上相似，但观察到乙硫醇氧化亲核捕获的反应性和区域选择性有所不同。这对仿生材料的设计和合成中这些天然结构单元及其衍生物的使用可能产生影响。

  DOI：

  10.1016/j.tet.2016.08.068

文献信息

• Attempts to Mimic Key Bond-Forming Events Associated with the Proposed Biogenesis of the Pentacyclic Lamellarins
  作者：Lorraine C. Axford、Kate E. Holden、Katrin Hasse、Martin G. Banwell、Wolfgang Steglich、Jörg Wagler、Anthony C. Willis

  DOI：10.1071/ch07402

  日期：——

  The pyrrole-tethered veratroles 16 and 27 each engage in PIFA-induced oxidative cyclization reactions to give compounds 22 and 29, respectively, which incorporate a key tricyclic fragment associated with the title natural products. In contrast, the corresponding catechols 11 and 12 only produce polymeric materials on subjection to analogous reaction conditions. Efforts to study lactone ring formation by the oxidative cyclization of catechol 30 and veratrole 38 have been thwarted by an inability to prepare the former substrate and decomposition of the latter. The reported conversions 44 → 45 and 46 → 47 suggest that a C2-carboxy group attached to the pyrrole ring can ‘direct’ the oxidative cyclization of N-tethered aryl groups. The acquisition of compound 22 by the means described herein provides an adventitious and concise route to the racemic modification of the pyrrolo[2,1-a]isoquinoline alkaloid crispine A (52).

  吡咯系链的藜芦烯 16 和 27 在 PIFA 诱导的氧化环化反应中分别生成化合物 22 和 29，其中包含了与标题天然产物相关的关键三环片段。相比之下，相应的儿茶酚 11 和 12 在类似的反应条件下只能生成聚合材料。由于无法制备儿茶酚 30 和 veratrole 38 的氧化环化反应底物以及后者的分解，研究内酯环形成的努力受挫。据报道，44 → 45 和 46 → 47 的转化过程表明，连接在吡咯环上的 C2-羧基可以 "引导 "N-系芳基的氧化环化。通过本文所述的方法获得化合物 22，为吡咯并[2,1-a]异喹啉生物碱 crispine A 的外消旋修饰（52）提供了一条简捷的途径。
• Oxidation of N-substituted dopamine derivatives: irreversible formation of a spirocyclic product
  作者：Edward J. Land、Almudena Perona、Christopher A. Ramsden、Patrick A. Riley

  DOI：10.1039/b505946a

  日期：——

  Oxidation of amide, urea and guanidinium derivatives of dopamine gives relatively stable ortho-quinones whereas oxidation of corresponding thioamide and amidinium derivatives rapidly and quantitatively gives novel bicyclic and spirocyclic products formed via the corresponding ortho-quinone.

  氧化多巴胺的酰胺、脲和胍衍生物可得到相对稳定的邻醌，而氧化相应的硫代酰胺和脒衍生物可快速定量地得到通过相应邻醌形成的新型双环和螺环产物。
• Model Insect Cuticle Sclerotization: Reactions of Catecholamine Quinones with the Nitrogen-Centered Nucleophiles Imidazole andN-Acetylhistidine
  作者：Xin Huang、Rongda Xu、M.Dale Hawley、Karl J. Kramer

  DOI：10.1006/bioo.1997.1065

  日期：1997.6

  The catecholamines N-acetyldopamine (NADA) and N-beta-alanyldopamine (NBAD) are two precursors for quinonoios used as sclerotizing agents in insect cuticle. This study focused on the reaction pathways of the quinones of NADA and NBAD by using two nitrogen-centered nucleophiles, imidazole and N-acetylhistidine, to model cuticular proteins containing histidyl residues. The quinones were prepared by electrochemical oxidation, using either a coulometric microcell or a how-through cell. The reactions of the quinones with the nucleophiles were investigated at physiological pH using electrochemical, chromatographic, and spectroscopic methods. The major products were purified by semipreparative Liquid chromatography and identified by mass spectrometry and nuclear magnetic resonance spectroscopy to be nucleophilic addition products of the quinones with the nucleophiles bonded to two carbons in the aromatic ring. The predominant products for both nucleophiles were C6 adducts of NADA and NBAD. C2 adducts of N-acetylhistidine were minor products. (C) 1997 Academic Press.
• Synthesis of catecholamine conjugates with nitrogen-centered bionucleophiles
  作者：Filipa Siopa、Alice S. Pereira、Luísa M. Ferreira、M. Matilde Marques、Paula S. Branco

  DOI：10.1016/j.bioorg.2012.05.002

  日期：2012.10

  The enzymatic (tyrosinase) and chemical (NaIO4, Ag2O or Fremys's salt) oxidation of biologically relevant catecholamines, such as dopamine (DA), N-acetyldopamine (NADA) and the Ecstasy metabolites (alpha-MeDA and N-Me-alpha-MeDA) generates the corresponding o-quinone which can be trapped with nitrogen bionucleophiles such as N-acetyl-histidine and imidazole in a regioselective reaction that takes place predominantly at the 6-position of the catecholamine. (C) 2012 Elsevier Inc. All rights reserved.
• Screening Test for Insecticides Interfering with Cuticular Sclerotization
  作者：Michael Londershausen、Andreas Turberg、Margarethe Spindler-Barth、Martin G. Peter

  DOI：10.1002/(sici)1096-9063(199612)48:4<315::aid-ps481>3.0.co;2-c

  日期：1996.12