o-bromobenzenediazonium | 17333-81-2

• 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: o-bromobenzenediazonium
• 英文别名: diazotiertes 2-Brom-anilin；o-Brom-benzoldiazonium；2-Brombenzoldiazonium；o-Brombenzoldiazonium；2-bromobenzenediazonium
• CAS: 17333-81-2
• 化学式: C₆H₄BrN₂
• 分子量: 184.015
• InChiKey: KHXDKIIBAAQQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  o-bromobenzenediazonium 在 三氯化砷 、 copper(I) bromide 作用下， 生成 o-bromophenylarsonic acid
  参考文献：
  名称：

  The Anticholinesterase Activity of Arylarsonic and Diarylarsinic Acids

  摘要：

  DOI：

  10.1021/ja01628a094

文献信息

• Could Stress Cause Psychosis in Individuals Vulnerable to Schizophrenia?
  作者：Cheryl Corcoran、Lilianne Mujica-Parodi、Scott Yale、David Leitman、Dolores Malaspina

  DOI：10.1017/s1092852900022240

  日期：2002.1

  It has long been considered that psychosocial stress plays a role in the expression of symptoms in schizophrenia (SZ), as it interacts with latent neural vulnerability that stems from genetic liability and early environmental insult. Advances in the understanding of the neurobiology of the stress cascade in both animal and human studies lead to a plausible model by which this interaction may occur: through neurotoxic effects on the hippocampus that may involve synaptic remodeling. Of late, the neurodevelopmental model of SZ etiology has been favored. But an elaboration of this schema that credits the impact of postnatal events and considers a role for neurodegenerative changes may be more plausible, given the evidence for gene-environment interaction in SZ expression and progressive structural changes observed with magnetic resonance imaging. Furthermore, new insights into nongliotic neurotoxic effects such as apoptosis, failure of neurogenesis, and changes in circuitry lead to an expansion of the time frame in which environmental effects may mediate expression of SZ symptoms.

  摘要长期以来，人们一直认为社会心理压力在精神分裂症（SZ）的症状表现中起着一定的作用，因为它与源于遗传和早期环境伤害的潜在神经脆弱性相互作用。在动物和人体研究中，人们对压力级联神经生物学的认识取得了进展，从而为这种相互作用的发生提供了一个可信的模型：通过对海马的神经毒性作用，可能涉及突触重塑。近来，SZ 病因的神经发育模式一直受到青睐。但是，考虑到在 SZ 表达中基因与环境相互作用的证据以及磁共振成像观察到的渐进性结构变化，对这一模式进行阐述，将出生后事件的影响考虑在内，并考虑神经退行性变化的作用，可能更加合理。此外，对神经细胞凋亡、神经元生成失败和电路变化等非神经胶质细胞毒性效应的新认识，扩大了环境影响可能介导 SZ 症状表达的时间范围。
• The effect of <i>ortho</i> and <i>para</i> substituents on the formation of the <i>E</i> and <i>Z</i> isomers of the arylhydrazones obtained from diazonium coupling with methyl 3-aminocrotonate and 3-aminocrotononitrile
  作者：Jason V. Jollimore、Marc Vacheresse、Keith Vaughan、Donald L. Hooper

  DOI：10.1139/v96-029

  日期：1996.2.1

  Reaction of arene diazonium salts with 3-aminocrotononitrile or methyl 3-aminocrotonate affords the 2-aryl-hydrazono-3-oxobutanenitrile (1 or 3 and 3′) or the methyl 2-arylhydrazono-3-oxobutanoate (2 and 2′ or 4 and 4′). A series of these hydrazones has been prepared with a range of electron-withdrawing and -donating substituents in the ortho or para position of the aryl moiety. The hydrazones have been characterized by spectroscopic methods, with emphasis on the ¹H NMR spectra, which have been used to determine the configuration of the hydrazones as E or Z or a mixture of the two. The para-substituted hydrazononitriles (1) are formed as a single species, namely the Z isomer, whereas the ortho isomers are formed as a mixture of E and Z configurations (3 and 3′). The hydrazonobutanoates (2 and 2′ or 4 and 4′) are formed as E/Z mixtures regardless of the position of the substituent in the aryl moiety. Complete assignments of all signals in the ¹H NMR spectra have been made on the basis of the ability of the various substituents to participate in intramolecular hydrogen bonding and a mechanism is proposed to account for the variations in the proportions of E and Z isomers and the effect of the nature of the substituent on this ratio. ¹³C NMR spectra of selected hydrazones have been recorded as an aid to structure assignment. Key words: hydrazone, diazonium, NMR spectroscopy, E/Z isomers, crotonic acid derivatives.

  芳香族重氮盐与3-氨基丙烯腈或甲基3-氨基丙烯酸酯反应，得到2-芳基-叠氮基-3-氧代丁腈（1或3和3'）或甲基2-芳基叠氮基-3-氧代丁酸酯（2和2'或4和4'）。已制备了一系列这些叠氮基化合物，其中芳基部分的邻位或对位具有一系列电子吸引或供给取代基。这些叠氮基化合物已通过光谱方法进行表征，重点放在¹H NMR谱上，该谱已用于确定叠氮基的构型为E或Z或两者的混合物。对位取代的叠氮基腈（1）形成为单一种类，即Z异构体，而邻位异构体形成为E和Z构型的混合物（3和3'）。叠氮基丁酸酯（2和2'或4和4'）无论芳基部分的取代基位置如何，都形成为E/Z混合物。基于各种取代基参与分子内氢键形成的能力，已对¹H NMR谱中所有信号进行了完整的指认，并提出了一种机制来解释E和Z异构体的比例变化以及取代基性质对此比例的影响。已记录了选定叠氮基的¹³C NMR谱，以帮助结构指认。关键词：叠氮基，重氮盐，NMR光谱，E/Z异构体，丙烯酸衍生物。
• Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones
  作者：Lorenzo Di Terlizzi、Simone Scaringi、Carlotta Raviola、Riccardo Pedrazzani、Marco Bandini、Maurizio Fagnoni、Stefano Protti

  DOI：10.1021/acs.joc.2c00225

  日期：2022.4.1

  The preparation of symmetrical (hetero)biaryls via arylazo sulfones has been successfully carried out upon visible light irradiation in the presence of PPh3AuCl as the catalyst. The present protocol led to the efficient synthesis of a wide range of target compounds in an organic-aqueous solvent under photocatalyst-free conditions.

  在PPh 3 AuCl作为催化剂的情况下，在可见光照射下成功地通过芳基偶氮砜制备了对称（杂）联芳基化合物。本方案可以在无光催化剂的条件下在有机水溶剂中有效合成多种目标化合物。
• METHOD FOR PRODUCING OPTICALLY ACTIVE 1,2-BIS(DIALKYLPHOSPHINO)BENZENE DERIVATIVE
  申请人：Tamura Ken

  公开号：US20130172597A1

  公开（公告）日：2013-07-04

  An industrially advantageous method for producing an optically active 1,2-bis(dialkylphosphino)benzene derivative of the present invention is provided. The method is characterized in that a phosphine-borane compound represented by the following general formula (1) is subjected to a deboronation reaction, followed by lithiation, then the reaction product is subjected to reaction with an alkyldihalogenophosphine represented by R a PX′ 2 , and thereafter the reaction product is subjected to reaction with a Grignard reagent represented by R b MgX″ to produce an optically active 1,2-bis(dialkylphosphino)benzene derivative (A). R 1 and R 2 respectively represent an alkyl group having 1 to 8 carbon atoms, and the number of carbon atoms is different between R 1 and R 2 . R a is either R 1 or R 2 and R b is the other of R 1 and R 2 . X, X′, and X″ each represent a halogen atom.

  本发明提供了一种在工业上具有优势的生产光学活性1,2-双(二烷基膦基)苯衍生物的方法。该方法的特征在于，将由下述一般式（1）表示的膦硼烷化合物进行脱硼反应，然后进行锂化反应，然后将反应产物与由RaPX′2表示的烷基二卤代膦烷发生反应，然后将反应产物与由RbMgX″表示的格氏试剂发生反应，以产生光学活性的1,2-双(二烷基膦基)苯衍生物（A）。R1和R2分别表示具有1至8个碳原子的烷基基团，且R1和R2之间的碳原子数不同。R为R1或R2中的一个，R为R1和R2中的另一个。X、X′和X″分别表示一个卤素原子。
• Fluoro oxindole derivatives as modulators of KCNQ potassium channels
  申请人：——

  公开号：US20020156120A1

  公开（公告）日：2002-10-24

  There is provided novel 3-fluoro-3-phenyl oxindole derivatives of Formula I 1 wherein R 1 , R 2 , R 3 and R 4 each are independently hydrogen, C 1-4 alkyl, halogen, fluoromethyl, trifluoromethyl, phenyl, 4-methylphenyl or 4-trifluoromethylphenyl; R 5 is C 1-6 alkyl optionally substituted with one to three same or different groups selected from fluoro and chloro, provided R 5 is not C 1-6 alkyl when Y is O; Y is O or S; and R 6 and R 7 each are independently hydrogen, chloro, bromo or trifluoromethy; which are openers of the KCNQ potassium channels and are useful in the treatment of disorders which are responsive to the opening of the KCNQ potassium channels.

  提供了一种新的式I1的3-氟-3-苯基吲哚衍生物，其中R1、R2、R3和R4各自独立地为氢、C1-4烷基、卤素、氟甲基、三氟甲基、苯基、4-甲基苯基或4-三氟甲基苯基；R5为C1-6烷基，可选地取代一到三个相同或不同的氟或氯基，但当Y为O时，R5不为C1-6烷基；Y为O或S；R6和R7各自独立地为氢、氯、溴或三氟甲基；它们是KCNQ钾通道的开放剂，可用于治疗对KCNQ钾通道开放有反应的疾病。