4-(氨基氧基)苯甲腈 | 94831-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(氨基氧基)苯甲腈
• 英文名称: O-(4-cyanophenyl)hydroxylamine
• 英文别名: 4-(aminooxy)benzonitrile；N-(p-cyanophenoxy)amine；4-Aminooxybenzonitrile
• CAS: 94831-79-5
• 化学式: C₇H₆N₂O
• mdl: MFCD21921059
• 分子量: 134.137
• InChiKey: KJYWSKLWGHSQEP-UHFFFAOYSA-N

物化性质

• 沸点：
  295.2±32.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(氨基氧基)苯甲腈 在 氯化锆(IV) 作用下， 以 硝基甲烷 、 水 、 乙腈 为溶剂， 反应 0.2h， 生成 邻氯苯腈
  参考文献：
  名称：

  用 ZrCl4 由芳基醛肟合成腈的新方法

  摘要：

  摘要 腈类很容易从相应的 O-苯基-或 O-(对氰基苯基)-醛肟与 ZrCl4 在硝基甲烷或苯中合成。

  DOI：

  10.1081/scc-120015406
• 作为产物：
  描述：

  4-羟基苯甲腈 在 potassium tert-butylate 、 2,4,6-三甲基苯磺酰羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以60.7%的产率得到4-(氨基氧基)苯甲腈
  参考文献：
  名称：

  Synthesis and opioid activities of some naltrexone oxime ethers

  摘要：

  A series of alkyl, cycloalkyl, aryl, and aralkyl ethers of naltrexone oxime was prepared. The compounds were examined in binding assays for mu, delta and kappa opioid receptor affinity. In addition, the naltrexone oxime ethers were studied in animal models that measure opioid agonist and antagonist activity. These studies led to the discovery of several compounds, notably phenethyl 3e and phenylpropyl 3f ethers of naltrexone, which have a 10-fold increase in potency at the kappa opioid receptor with potent mu and kappa agonist properties in vivo.

  DOI：

  10.1016/0223-5234(94)90027-2

文献信息

• Fluorous Tagged <i>N</i>-Hydroxy Phthalimide for the Parallel Synthesis of <i>O</i>-Aryloxyamines
  作者：Florence S. Gaucher-Wieczorek、Ludovic T. Maillard、Bernard Badet、Philippe Durand

  DOI：10.1021/cc100098v

  日期：2010.9.13

  The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi’s method. A library of O-aryloxyamines

  在药物化学和基于片段的方法领域中，O-芳氧基胺的平行合成仍未满足。为了填补这一空白，采用了一种溶液阶段两步法，该方法基于（1）铜催化的芳基硼酸与带有氟标记的N-羟基邻苯二甲酰亚胺的交叉偶联，以及（2）使用Taguchi方法设计并优化了负载型氨解反应。以高产率，高纯度和多样性合成了O-芳氧基胺的文库。
• Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C–H Alkylation and Amidation Reactions of <i>N</i>-Phenoxyacetamides
  作者：Yunxiang Wu、Zhaoqiang Chen、Yaxi Yang、Weiliang Zhu、Bing Zhou

  DOI：10.1021/jacs.7b10349

  日期：2018.1.10

  diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization

  已经在温和和氧化还原中性条件下开发了 Rh(III) 催化的 N-苯氧基乙酰胺与重氮化合物的不对称 CH 烷基化和酰胺化，产生二氮作为唯一的副产物。该反应代表了两个邻 CH 键的一步不对称双官能化的第一个例子。实验和计算研究支持 N-苯氧基乙酰胺最有可能通过 Rh(III) 催化的 CH 活化与重氮化合物进行初始邻位 CH 烷基化，所得的 Rh(III) 中间体随后经历分子内氧化加成到 ON 键形成 Rh(V) 氮烯类物质，该物质被质子化并进一步指向苯环的第二个邻位的亲电加成。
• Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition-Metal-Free Hydroamination and <i>N</i>-Arylation Reactions
  作者：Jacob Davies、Thomas D. Svejstrup、Daniel Fernandez Reina、Nadeem S. Sheikh、Daniele Leonori

  DOI：10.1021/jacs.6b04920

  日期：2016.7.6

  The development of photoredox reactions of aryloxy-amides for the generation of amidyl radicals and their use in hydroamination-cyclization and N-arylation reactions is reported. Owing to the ease of single-electron-transfer reduction of the aryloxy-amides, the organic dye eosin Y was used as the photoredox catalyst, which results in fully transition-metal-free processes. These transformations exhibit

  报道了芳氧基-酰胺光氧化还原反应产生酰胺基自由基的发展及其在加氢胺化-环化和 N-芳基化反应中的应用。由于芳氧基酰胺易于单电子转移还原，有机染料伊红 Y 被用作光氧化还原催化剂，这导致完全无过渡金属的过程。这些转变表现出广泛的范围，可以容忍几个重要的功能，并已用于复杂和高价值含氮分子的后期修饰。
• Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
  作者：Jacob Davies、Samuel G. Booth、Stephanie Essafi、Robert A. W. Dryfe、Daniele Leonori

  DOI：10.1002/anie.201507641

  日期：2015.11.16

  formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O‐aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique

  通过设计一类新型的反应性O-芳基肟实现了亚胺基在新型和不同的加氢和亚氨基羟基化环化反应中的形成和使用。由于它们的低还原电位，廉价的有机染料曙红Y可以用作有机催化加氢反应的光催化剂。此外，还确定了独特的亚氨基羟基化反应的条件。从肟和Et 3 N的新型电子供体-受体复合物中可见光介导的电子转移被认为是该过程的关键步骤。
• CHROMOPHORES FOR PHOTOCHROMIC COMPOSITIONS USEFUL FOR THREE DIMENSIONAL DISPLAY APPLICATIONS
  申请人：Gu Tao

  公开号：US20170044373A1

  公开（公告）日：2017-02-16

  Described herein are novel azo-benzene type chromophores. The chromophores are useful in photochromic compositions comprising a polymer matrix and a chromophore, wherein the chromophore is a novel azo-benzene type structure. The photochromic composition is photoresponsive upon irradiation by at least one wavelength of laser light across the visible light spectrum. Photochromic devices which comprise the novel azo-benzene type chromophore compound show significantly higher photoinduced birefringence, higher diffraction efficiency, and brighter images than devices that comprise well known azo-benzene chromophores. The photochromic composition may include a liquid crystal.

  本文描述了一种新型的偶氮苯类色团。这些色团在包括聚合物基质和色团的光致变色组合物中具有用途，其中色团是一种新型的偶氮苯类结构。所述光致变色组合物在可见光谱范围内至少一个激光光波长的照射下具有光响应性。包含新型偶氮苯类色团化合物的光致变色器件显示出比包含众所周知的偶氮苯色团的器件具有显著更高的光诱导双折射、更高的衍射效率和更亮的图像。光致变色组合物可能包括液晶。