1-(4-溴苯基)-2-硝基乙烷 | 137521-07-4

• 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: 1-(4-溴苯基)-2-硝基乙烷
• 英文名称: 1-(4-bromophenyl)-2-nitroethane
• 英文别名: 1-Bromo-4-(2-nitroethyl)benzene
• CAS: 137521-07-4
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: LGJIRZABHAPNNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-溴苯基)-2-硝基乙烷 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 三乙烯二胺 、 sodium acetate 、 对甲苯磺酸 、 苯甲酸 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 生成 (2R,3R,3aR,5R,7aS)-5-(4-bromobenzyl)-2-methoxy-5-nitro-3-(nitromethyl)-hexahydro-2H-furo[2,3-b]pyran
  参考文献：
  名称：

  结构复杂的环半缩醛和功能化的硝基烯烃的不对称有机催化顺序反应，以合成不同的杂环。

  摘要：

  以简洁的方式制备了具有外消旋四取代的立体中心的结构复杂的环状半缩醛，并将其成功地用于有机催化对映选择性序列中，与官能化的硝基烯烃反应，从而提供了含双环缩醛的化合物，作为两种可分离的差向异构体，具有出色的立体选择性。该反应显示出相对于起始半缩醛而言较宽的底物范围。而且，该方案允许将产物合成转化为具有实质性结构多样性和广泛功能性的各种有趣的杂环化合物。

  DOI：

  10.1021/acs.orglett.8b01386
• 作为产物：
  描述：

  对溴苯甲醛 在 sodium tetrahydroborate 、 silica gel 、 环己胺 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 6.33h， 生成 1-(4-溴苯基)-2-硝基乙烷
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

  摘要：

  Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.054

文献信息

• Organocatalytic Biomimetic Reduction of Conjugated Nitroalkenes
  作者：Peter Schreiner、Zhiguo Zhang

  DOI：10.1055/s-2007-983805

  日期：2007.8

  A thiourea-catalyzed biomimetic reduction of conjugated nitroalkenes has been developed. Various aromatic and aliphatic conjugated nitroalkenes can be reduced to give the respective nitroalkanes with good yields under mild conditions. This protocol is not only practical, but may also provide insight into the mechanisms of redox transformations in biological systems.

  已经开发了一种硫脲催化的共轭硝基烯烃的仿生还原。各种芳香族和脂肪族共轭硝基烯烃可以在温和条件下以良好的产率还原得到相应的硝基烷烃。该协议不仅实用，而且还可以深入了解生物系统中氧化还原转化的机制。
• Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃
  作者：Chiara Faverio、Monica Fiorenza Boselli、Patricia Camarero Gonzalez、Alessandra Puglisi、Maurizio Benaglia

  DOI：10.3762/bjoc.17.83

  日期：——

  Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH₃NH₃, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

  深共熔溶剂（DESs）作为传统有机溶剂的绿色、安全、经济和环境可持续替代品已引起关注。在这里，我们报告了将原子经济、非常方便和廉价的试剂BH₃NH₃与基于生物的共熔混合物结合在一起，作为生物可再生溶剂，用于合成硝基烷烃，这是氨基的宝贵前体。各种硝基苯乙烯和烷基取代硝基烯烃，包括α-和β-取代硝基烯烃，均可选择性地还原为硝基烷烃，采用以原子经济为导向的简单方便的实验程序。建立了一种可靠且易于重复的协议，用于在不使用任何有机溶剂的情况下分离产品，并成功地研究了DES混合物的可回收性。
• PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
  申请人：Tanaka Keigo

  公开号：US20090082403A1

  公开（公告）日：2009-03-26

  Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R 1 represents hydrogen, halogen, amino, R 11 —NH— wherein R 11 represents C 1-6 alkyl, hydroxy C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, or C 1-6 alkoxycarbonyl C 1-6 alkyl, R 12 —(CO)—NH— wherein R 12 represents C 1-6 alkyl group or C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkyl, hydroxy C 1-6 alkyl, cyano C 1-6 alkyl, C 1-6 alkoxy, or C 1-6 alkoxy C 1-6 alkyl or a phosphonoamino group; R 2 represents hydrogen, C 1-6 alkyl, amino, or a di C 1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C 1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, —CH 2 O—, —OCH 2 —, —NH—, —CH 2 NH—, —NHCH 2 —, —CH 2 S—, or —SCH 2 —; R 3 represents hydrogen or halogen or C 1-6 alkyl, C 3-8 cycloalkyl, C 6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R 4 represents hydrogen or halogen; provided that either R 1 or R 2 represents a phosphonoamino group.

  抗真菌剂具有优异的抗真菌作用物理化学性质，包括安全性和水溶性。化合物由式（I）表示，或其盐： 其中R1代表氢，卤素，氨基，R11—NH—其中R11代表C1-6烷基，羟基C1-6烷基，C1-6烷氧基C1-6烷基，或C1-6烷氧羰基C1-6烷基，R12—（CO）—NH—其中R12代表C1-6烷基或C1-6烷氧基C1-6烷基，C1-6烷基，羟基C1-6烷基，氰基C1-6烷基，C1-6烷氧基，或C1-6烷氧基C1-6烷基或磷酰氨基团；R2代表氢，C1-6烷基，氨基，或二C1-6烷基氨基团或磷酰氨基团；X和Y中的一个是氮，另一个是氮或氧；环A代表5-或6-成员杂芳基环或可能具有卤素原子或1或2个C1-6烷基基团的苯环；Z代表单键，亚甲基基团，乙烯基团，氧，硫，—CH2O—，—OCH2—，—NH—，—CH2NH—，—NHCH2—，—CH2S—，或—SCH2—；R3代表氢或卤素或C1-6烷基，C3-8环烷基，C6-10芳基，5-或6-成员杂芳基团或可能具有1或2个取代基的5-或6-成员非芳香杂环基；和R4代表氢或卤素；前提是R1或R2中的一个代表磷酰氨基团。
• Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
  申请人：Tanaka Keigo

  公开号：US20070105904A1

  公开（公告）日：2007-05-10

  An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R 1 represents a hydrogen atom, a halogen atom, an amino group, a C 1-6 alkyl group, a C 1-6 alkoxy group or a C 1-6 alkoxy C 1-6 alkyl group; R 2 represents a hydrogen atom, a C 1-6 alkyl group, an amino group or a di C 1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C 1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH 2 O—, —OCH 2 —, —NH—, —CH 2 NH—, —NHCH 2 —, —CH 2 S—, or —SCH 2 —; R 3 represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R 4 represents a hydrogen atom or a halogen atom.

  本发明的一个目的是提供一种具有优异的抗真菌效果并在其物理性质、安全性和代谢稳定性方面优越的抗真菌剂。根据本发明，公开了以下式(I)所代表的化合物或其盐： 其中R1代表氢原子、卤素原子、氨基、C1-6烷基、C1-6烷氧基或C1-6烷氧基C1-6烷基；R2代表氢原子、C1-6烷基、氨基或二C1-6烷基氨基中的一个；X和Y中的一个是氮原子，另一个是氮原子或氧原子；环A代表一个5-或6-成员杂芳基环或可能具有卤素原子、1个或2个C1-6烷基的苯环；Z代表一个单键、一个亚甲基基、一个乙烯基、一个氧原子、一个硫原子、-CH2O-、-OCH2-、-NH-、-CH2NH-、-NHCH2-、-CH2S-或-SCH2-；R3代表氢原子、卤素原子、C1-6烷基、C3-8环烷基、C6-10芳基、一个5-或6-成员杂芳基、或可能具有1个或2个取代基的5-或6-成员非芳香杂环基；R4代表氢原子或卤素原子。
• O₂-Mediated Oxidation of Aminoboranes through 1,2-N Migration
  作者：Marian Rauser、Daniel P. Warzecha、Meike Niggemann

  DOI：10.1002/anie.201803168

  日期：2018.5.14

  In analogy to the classical reaction of C−B bonds with peroxides, the first oxidative functionalization of aminoboranes through a 1,2‐N migration was realized. Readily available aliphatic nitro compounds are thereby transformed into N‐ and O‐functionalized hydroxylamines in a single synthetic operation. Addition of hazardous peroxides is avoided. Instead, the insertion of O2, as the terminal oxidant

  类似于C-B键与过氧化物的经典反应，通过1,2-N迁移实现了氨基硼烷的第一个氧化功能化。易于获得的脂肪族硝基化合物可通过一次合成操作转化为N和O功能化的羟胺。避免添加有害的过氧化物。相反，将O 2作为末端氧化剂插入Zn-C键可提供必要的过氧化物。反过来，所需的锌有机基团是通过硼与锌的交换，由硝基向氨基硼烷转化的有机硼酸酯副产物形成的。