1-methylthio-4-(2-nitroethyl)benzene | 951386-14-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methylthio-4-(2-nitroethyl)benzene
• 英文别名: methyl(4-(2-nitroethyl)phenyl)sulfane；1-(4-methylthiophenyl)-2-nitroethane；1-(Methylthio)-4-(2-nitroethyl)benzene；1-methylsulfanyl-4-(2-nitroethyl)benzene
• CAS: 951386-14-4
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: JWAZCXVXGYZBRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  337.8±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methylthio-4-(2-nitroethyl)benzene 在 吡啶 、 盐酸 、 potassium fluoride 、 水 、 盐酸二甲胺 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 39.0h， 生成 2-N-acetylamino-1,3-di(4-methylthiophenyl)propane
  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
• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 在 sodium tetrahydroborate 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.67h， 生成 1-methylthio-4-(2-nitroethyl)benzene
  参考文献：
  名称：

  硝基脂族衍生物抑制LDL氧化和炎性体组装。潜在用作抗炎和抗动脉粥样硬化剂

  摘要：

  先前我们已经显示了几种对位取代的芳基硝基烯烃的抗氧化和抗炎特性。由于氧化应激和炎症是驱动动脉粥样硬化发生和发展的关键过程，因此在本工作中，研究了芳基-硝基脂肪族衍生物（包括几种新设计的硝基烷烃）扩展文库的抗氧化，抗炎和抗动脉粥样硬化特性。 。使用氧自由基吸收能力测定（ORAC）测量的硝基脂肪族化合物的抗氧化能力表明，对-甲基硫代苯基衍生物在防止荧光素氧化方面比Trolox有效约三倍，而与硝基附近是否存在双键无关。对-二甲基氨基苯基衍生物的过氧自由基清除剂容量甚至更高，因为这些化合物的还原形式甚至更具活性。实际上，1-二甲氨基-4-（2-硝基-1Z-乙烯基）苯和1-二甲氨基-4-（2-硝基-1Z-丙烯基）苯的抗氧化能力为4.2±0.1和5.4±0.1 Trolox当量/摩尔；用乙基和丙基衍生物获得的ORAC值分别为10±1和13±2 Trolox Eq / mol。该P-二甲基氨基衍生物，尤

  DOI：

  10.1016/j.ejmech.2018.09.062

文献信息

• 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。
• Direct Reductive <i>N</i> -Functionalization of Aliphatic Nitro Compounds
  作者：Marian Rauser、Christoph Ascheberg、Meike Niggemann

  DOI：10.1002/chem.201705986

  日期：2018.3.15

  direct reductive N‐functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic

  提出了脂族硝基化合物直接还原N-官能化的第一个通用方案。硝基通过B 2 pin 2和锌有机基的温和且容易获得的组合而部分还原为类固醇。因此，避免了不稳定的亚硝基中间体的形成，到目前为止，该中间体已经严重限制了脂肪族硝基化合物的还原转化。该反应通过锌有机基的亲电胺化而结束。
• Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water
  作者：Dong Xu、Yang Chen、Changmeng Liu、Jiaxi Xu、Zhanhui Yang

  DOI：10.1039/d1gc01907d

  日期：——

  An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20 000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as

  在非常低的催化剂负载量（S/C = 高达 10000 或 20 000）下，使用甲酸或甲酸钠作为水中的无痕氢化物供体，实现了铱催化的高化学选择性和高效转移氢化还原结构多样的硝基烯烃。还观察到优异的功能耐受性。催化剂的周转次数和周转频率高达18 600和19 200 h -1， 分别。不需要惰性气氛保护。硝基烯烃的反应性取决于它们的取代模式，pH 值是实现完全转化和优异化学选择性的关键因素。产品的纯化通过简单的萃取实现，无需柱层析。还原过程在 10 000 S/C 比率下轻松放大到 10 g 规模。这种绿色还原在对映选择性氢化中的潜力已经得到证实。
• Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
  作者：Suzanne M. Cloonan、John J. Keating、Desmond Corrigan、John E. O’Brien、Pierce V. Kavanagh、D. Clive Williams、Mary J. Meegan

  DOI：10.1016/j.bmc.2010.04.022

  日期：2010.6.1

  drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and structural identification of a number of novel pyridines, dihydropyridone and N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro cytotoxicity of 4-MTA, its synthesis byproducts together

  4-甲硫基苯丙胺（4-MTA）被认为是一种3,4-亚甲二氧基甲基苯丙胺（MDMA）滥用药物。这种苯丙胺类药物通常含有不受控制的非法秘密合成过程的副产物。我们报告了许多新型吡啶，二氢吡啶酮和N，N的分离和结构鉴定-二（1-芳基-2-丙基）胺是与4-MTA和相关苯丙胺的秘密合成有关的途径特定的副产物。我们报告了4-MTA的体外细胞毒性，其合成副产物与一些结构相关的硫取代的α-烷基苯乙胺在过度表达人单胺转运蛋白的细胞系以及主要神经元细胞系模型和多巴胺能神经母细胞瘤细胞系中。在药理定义的浓度范围内，发现4-MTA以及许多其他与结构相关的苯丙胺衍生物和合成杂质对这些细胞具有细胞毒性，这表明4-MTA在体外是细胞毒性剂，因此可能具有神经毒性剂的潜力。体内。
• Preparation of β-phenylnitroethanes having electron-donating aryl substitution
  作者：Frederick A. Luzzio、Marek T. Wlodarczyk、Damien Y. Duveau、Juan Chen

  DOI：10.1016/j.tetlet.2007.07.098

  日期：2007.9

  beta-Phenyl-beta-hydroxynitroethanes having activating aryl substituents are treated with triethylsilane/trifluoroacetic acid under solventless conditions to give the corresponding phenyinitroethanes. Substrates having no aryl substituents or substituents that are only mildly activating or deactivating do not result in appreciable conversion to the title compounds. (c) 2007 Elsevier Ltd. All rights reserved.