1,2-(4-bromo-2-nitrophenyl)ethane | 873988-08-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-(4-bromo-2-nitrophenyl)ethane
• 英文别名: 1,2-bis(4-bromo-2-nitrophenyl)ethane
• CAS: 873988-08-0
• 化学式: C₁₄H₁₀Br₂N₂O₄
• 分子量: 430.052
• InChiKey: BHPDJIFUYNCXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-(4-bromo-2-nitrophenyl)ethane 在 sodiumsulfide nonahydrate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以52%的产率得到6,6'-(ethane-1,2-diyl)bis(3-bromoaniline)
  参考文献：
  名称：

  控制激酶抑制剂与光的共价反应

  摘要：

  共价激酶抑制剂是最近进入临床的一些最成功的药物，还有许多其他药物处于临床前开发阶段。一种常见的策略是使用丙烯酰胺亲电试剂靶向 ATP 结合位点附近的半胱氨酸。为了增加激酶抑制剂的组织选择性，控制这些亲电子试剂与光的反应性可能是有利的。在这里，我们介绍了激酶 JNK3 的共价抑制剂，它们起着光开关亲和标签 (PAL) 的作用。我们的先导化合物含有重氮辛光开关，在黑暗中是不良的非共价抑制剂，在可见光照射后成为有效的共价抑制剂。

  DOI：

  10.1002/anie.202103767
• 作为产物：
  描述：

  4-甲基-3-硝基苯胺 在 乙醚 、 氢溴酸 、 sodium ethanolate 、 亚硝酸异戊酯 作用下， 生成 1,2-(4-bromo-2-nitrophenyl)ethane
  参考文献：
  名称：

  Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism

  摘要：

  The etiologic diagnosis of hirsutism is often difficult. Previous studies have reported normal basal androgen and SHBG concentrations in 33-50% of hirsute women, suggesting the presence of an "idiopathic" form of hirsutism as the most frequent cause of this problem. The recent use of GnRH-analogues together with the corticotropin stimulation test allows better understanding of whether the cause of hirsutism is androgen excess and, if so, whether the origin of the latter is ovarian, adrenal or both. The present study evaluated adrenal and ovarian function in 48 young hirsute women as well as in 78 normal women matched for body mass index and age, who acted as control group. To determine ovarian function, a single 100-mug dose of GnRH analogue triptorelin was injected sc; thereafter, gonadotropins, 17-hydroxyprogesterone (17-OHP), Delta4-androstenedione (Delta4), total testosterone (T) and estradiol were determined. To better understand the adrenal function, 250 mug of 1,24 ACTH were administrated as iv infusion for 5 h, and plasma cortisol (F), 17-OHP, Delta4, DHEAS, T, 11-desossicortisol were measured. The combined use of these two stimulation tests was able to detect mild to moderate abnormalities in the steroidogenesis of ovaries alone (23%), adrenals alone (16.6%), or both (35.4%) in most hirsute women (75%) with otherwise normal baseline androgen concentrations. In particular, patients showed significantly increased responses of 17-OHP, Delta4, total T, 11-desossicortisol, and F to 1,24-ACTH administration. Moreover, they also had significantly higher 17-OHP and T responses to triptorelin. In conclusion, milder forms of functional ovarian and/or adrenal hyperandrogenism, similar to those found in clearly hyperandrogenic women, were observed and could be an underlying mechanism of idiopathic hirsutism. (J. Endocrinol. Invest. 24: 491-498, 2001) (C) 2001, Editrice Kurtis.

  DOI：

  10.1007/bf03343881

文献信息

• Effect of non-planarity on the spin distribution in the radical anions containing the stilbene or the azobenzene ?-system: An ESR and ENDOR Study
  作者：Fabian Gerson、Axel Lamprecht、Markus Scholz、Heinz Troxler、Dieter Lenoir

  DOI：10.1002/hlca.19960790130

  日期：1996.2.7

  group. This finding is impressively demonstrated by the similar hyperfine data for 9· − and 11· − which contrast with the strongly highly hindered 13· −. A. plausible interpretation is readily provided by the electron affinities of the constituent π-moieties in stilbene and azobenzene. While those of benzene and ethene are both comparatively low, the azo group has a considerably higher electron affinity

  5 H-二苯并[ a，d ]环庚烯（9），5 H-二苯并[ c，f ] [1,2]二氮杂（10），5,6-二氢二苯并[ a，e ]环辛烯（11）的自由基阴离子），5,6-二氢二苯并[ c，g ] [1,2]重氮（12）和（E）-2,2,2,5,5-四甲基-3,4-二苯基己-3-烯（13））通过ESR和ENDOR光谱进行表征。将它们的超细数据与先前报道的也包含二苯乙烯或偶氮苯π系统的自由基阴离子的数据进行了比较。1,2-二苯乙烯系列自由基阴离子中的π-自旋分布仅对π-系统与平面的偏离有中等敏感性，而偶氮苯系列的自由基阴离子则通过将π-自旋从苯环移开来响应空间应变。偶氮基团。相似的9 ·−和11 ·−超精细数据证明了这一发现，这与强烈受阻的13 ·−相反。通过二苯乙烯和偶氮苯中的组成π-部分的电子亲和力可以容易地提供一种合理的解释。尽管苯和乙烯的相对较低，但偶氮基团的电子亲和力较高。
• Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence
  作者：Qian Zhu、Suning Wang、Pangkuan Chen

  DOI：10.1021/acs.orglett.9b01215

  日期：2019.6.7

  π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C2-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for

  据报道，π共轭的偶氮苯衍生物使偶氮部分与芳基荧光团偶联。使用C 2桥连的偶氮苯的光化学，我们完成了两个基于重氮基的光开关分子（cAz1和cAz2）。除了显着的光致变色特性外，它们还显示出开启的荧光，并且随着cAz1的量子效率提高到0.22，发光得到了极大的增强。辐射持续存在，只能通过热停用将其关闭。与线性类似物（Az1 – Az4）。这项工作可以为使用光开关系统的高级发光材料提供新的支架。
• Synthetic Photoswitchable Neurotransmitters Based on Bridged Azobenzenes
  作者：Gisela Cabré、Aida Garrido-Charles、Àngels González-Lafont、Widukind Moormann、Daniel Langbehn、David Egea、José M. Lluch、Rainer Herges、Ramon Alibés、Félix Busqué、Pau Gorostiza、Jordi Hernando

  DOI：10.1021/acs.orglett.9b01222

  日期：2019.5.17

  Photoswitchable neurotransmitters of iono-tropic kainate receptors were synthesized by tethering a glutamate moiety to disubstituted C2-bridged azobenzenes, which were prepared through a novel methodology that allows access to diazocines with higher yields and versatility. Because of the singular properties of these photochromes, photoisomerizable compounds were obtained with larger thermal stability for their inert cis isomer than for their biologically activity trans state. This enabled selective neuronal firing upon irradiation without background activity in the dark.