anthranilonitrile hydrochloride | 6944-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: anthranilonitrile hydrochloride
• 英文别名: 2-aminobenzonitrile hydrochloride；2-cyanophenylamine hydrochloride；aminobenzonitrile hydrochloride；2-cyanoaniline hydrochloride；o-cyanoaniline hydrochloride；o-Cyanoaniline hydrochloride；(2-cyanophenyl)azanium;chloride
• CAS: 6944-57-6
• 化学式: C₇H₆N₂*ClH
• 分子量: 154.599
• InChiKey: PKJKEAPSCKXNEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  10
• 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：
  49.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  anthranilonitrile hydrochloride 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-(2-Cyano-phenyl)-3-pyridin-4-yl-urea
  参考文献：
  名称：

  N-Phenyl-N'-pyridinylureas as anticonvulsant agents

  摘要：

  A series of N-phenyl-N'-pyridinylureas was examined for anticonvulsant activity. Extensive structure/activity investigations revealed optimal activity in the N-(2,6-disubstituted-phenyl)-N'-(4-pyridinyl)urea series, with 37 exhibiting the best overall anticonvulsant profile. Compound 37 was effective against seizures induced by maximal electroshock but did not protect mice from clonic seizures produced by the convulsant pentylenetetrazol. The overall pharmacological profile suggests that 37 would be of therapeutic use in the treatment of generalized tonic-clonic and partial seizures. Compound 37 was selected for Phase 1 clinical trials.

  DOI：

  10.1021/jm00164a061
• 作为产物：
  描述：

  2-硝基苯甲腈 在 盐酸 、 [Fe{N(SiMe₃)₂}(4,5-bis(silylene)-2,7,9,9-tetramethyl-9H-acridin-10-ide)] 作用下， 以 乙醚 、 氘代苯 、 水 为溶剂， 反应 12.0h， 生成 anthranilonitrile hydrochloride
  参考文献：
  名称：

  以双(N-杂环亚甲硅烷基)氨基铁配合物为催化剂对一氧化二氮和硝基化合物的脱氧

  摘要：

  报道了在温和条件下通过明确的双（亚硅基）氨基铁络合物将 N 2 O高效催化降解为 N 2 ，这涉及铁和亚硅基配体之间的协同作用。已经使用相同的方法开发了将硝基化合物选择性还原为具有良好官能团耐受性和优异化学选择性的氨基硼烷。

  DOI：

  10.1002/anie.202114598

文献信息

• Steric hindrance as a key factor on proton transfer in the σ-adduct forming reactions of o-substituted anilines with 1,3,5-trinitrobenzene in dimethylsulfoxide
  作者：Basim H. Asghar

  DOI：10.1007/s00706-008-0913-5

  日期：2008.10

  Kinetic and equilibrium studies are reported of the reactions of 1,3,5-trinitrobenzene ( TNB ) with a series of o -substituted anilines in dimethyl sulfoxide ( DMSO ) in the presence of 1,4-diazabicyclo[2.2.2.]octane ( DABCO ). The pK a values in DMSO for the aniline derivatives were measured using the proton-transfer equilibrium with 2,4-dinitrophenol. Kinetic studies are compatible with a two-step

  动力学和平衡研究报告了1,3,5-三硝基苯（ TNB ）与一系列 邻 取代苯胺在二甲亚砜（ DMSO ）中在1,4-二氮杂双环[2.2.2]辛烷存在下的反应。 （ DABCO ）。使用与2,4-二硝基苯酚的质子转移平衡来测量 DMSO 中苯胺衍生物的 pK a 值 。动力学研究与两步过程兼容，该过程涉及胺对 TNB 的初始亲核攻击， 从而生成两性离子中间体，该中间体可能将酸性质子转移至 DABCO 产生阴离子产物。结果表明在涉及2，6-二取代苯胺的反应中，质子转移存在空间位阻。
• Synthesis and benzodiazepine binding activity of a series of novel [1,2,4]triazolo[1,5-c]quinazolin-5(6H)-ones
  作者：John E. Francis、William D. Cash、Beverly S. Barbaz、Patrick S. Bernard、Richard A. Lovell、Gerard C. Mazzenga、Robert C. Friedmann、James L. Hyun、Albert F. Braunwalder

  DOI：10.1021/jm00105a044

  日期：1991.1

  Investigation of tricyclic heterocycles related to the 2-arylpyrazolo[4,3-c]quinolin-3(5H)-ones, structures with high affinity for the benzodiazepine (BZ) receptor, led to the synthesis of 2-phenyl-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one, a compound with 4 nM binding affinity to the BZ receptor. Analogues were prepared to assess the importance of the 2-substituent and ring substitution in modifying

  对与2-芳基吡唑并[4,3-c]喹啉-3（5H）-ones相关的三环杂环的研究，对苯二氮卓（BZ）受体具有高亲和力的结构导致了2-苯基-[1， 2,4] triazolo [1,5-c] quinazolin-5（6H）-one，一种对BZ受体具有4 nM结合亲和力的化合物。制备类似物以评估2-取代基和环取代在修饰活性中的重要性。设计了几种新颖的合成路线来制备目标化合物，包括从蒽腈和酰肼开始的两步合成。在该系列筛选的34种化合物中，在大鼠模型中发现3种化合物是有效的BZ拮抗剂。前导化合物9-氯-2-（2-氟苯基）[1,2,4]三唑并[1,5-c]喹唑啉-5（6H）-一（CGS 16228），
• Microwave-Assisted Synthesis of Arylazoaminopyrazoles as Disperse Dyes for Textile Printing
  作者：Tawfik A. Khattab、Karima M. Haggag、Mohamed H. Elnagdi、Amal A. Abdelrahman、Sherif Abdelmoez Aly

  DOI：10.1002/zaac.201600148

  日期：2016.6

  The synthesis of heterocyclic azo-dyes via conventional heating and microwave (MW) heating was investigated. From a sequence of reactions starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamines and 4-arylazo-2-phenyl-2H-pyrazol-3-ylamines were obtained. The structures these compounds were obtained by inspection of spectroscopic and analytical techniques including 1H and 13C NMR spectroscopy

  研究了通过常规加热和微波 (MW) 加热合成杂环偶氮染料。从从氰基乙酸开始的一系列反应中，获得了 4-芳基偶氮-2H-吡唑-3-基胺和 4-芳基偶氮-2-苯基-2H-吡唑-3-基胺。这些化合物的结构是通过检查光谱和分析技术获得的，包括 1H 和 13C NMR 光谱、IR 光谱、质谱和元素分析。研究了这些分散染料在印花涤纶织物中的牢度性能和紫外/可见吸收光谱数据。
• Synthesis and spectral properties of symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyestuffs for dyeing polyester fabrics
  作者：Tawfik Khattab、Karima M. Haggag

  DOI：10.21608/ejchem.2017.1479.1103

  日期：2017.12.1

  In this study, we report on a general synthetic approach to both symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyes. The reaction of enaminonitrile with aromatic diazonium salts in slightly acidic medium affords arylhydrazonals as stable intermediate that are readily converted into asymmetrical formazans via second azo-coupling in a weak alkaline medium. Symmetrical formazan dyestuffs are synthesized directly via double azo-coupling of the key intermediate 3-piperidinylacrylonitrile with the corresponding diazonium salts in weak alkaline medium using sodium acetate as a weak base. The structures of the prepared dyestuffs and intermediates are demonstrated by elemental analysis (C, H, N), 1H and 13C NMR, FTIR and GC-MS spectroscopic techniques. The prepared formazan disperse colorants are applied to dye polyester fabric to give satisfactory fastness properties to wash, perspiration, rubbing and light.

  在本研究中，我们报告了一种合成对称和非对称3-氰基-1,5-二芳基福尔马赞染料的普遍合成方法。酰胺氰与芳香族重氮盐在稍微酸性的介质中反应，生成作为稳定中间体的芳基肼醛，这些中间体可以通过在弱碱介质中进行二次偶氮偶联反应，转化为非对称福尔马赞。对称福尔马赞染料则通过将关键中间体3-哌啶基丙烯腈与相应的重氮盐在弱碱性介质中进行双偶氮偶联反应直接合成，采用醋酸钠作为弱碱。通过元素分析（C、H、N）、1H和13C NMR、FTIR和GC-MS光谱技术证明所制备染料和中间体的结构。所制备的福尔马赞分散色料应用于聚酯面料的染色，获得良好的洗涤、汗液、摩擦和光照的牢度性能。
• Cyanamides in cyclization reactions with anthranilates, 2-aminophenyl ketones, and methyl 2-(3-oxopiperazin-2-yl)acetate
  作者：Kh. S. Shikhaliev、A. S. Shestakov、S. M. Medvedeva、N. V. Gusakova

  DOI：10.1007/s11172-008-0025-8

  日期：2008.1

  Cyclization of aryl-, aroyl-, and (4,6-dimethylpyrimidin-2-yl)cyanamides with methyl anthranilates, 2-aminophenyl ketones, and methyl 2-(3-oxopiperazin-2-yl)acetate leads to 2-amino-3,4-dihydroquinazolin-4-one, 2-aminoquinazoline, and 6-amino-1,3,4,8,9,9a-hexahydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione derivatives, respectively.

  芳基-、芳酰基-和（4,6-二甲基嘧啶-2-基）氰胺与邻氨基苯甲酸甲酯、2-氨基苯基酮和2-（3-氧代哌嗪-2-基）乙酸甲酯环化生成2-氨基- 3,4-二氢喹唑啉-4-one、2-氨基喹唑啉和6-氨基-1,3,4,8,9,9a-六氢-2H-吡嗪并[1,2-c]嘧啶-1,8-二酮衍生品，分别。