2-(2,4-Dichlorphenyl)nitroaethan | 72538-34-2

• 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: 2-(2,4-Dichlorphenyl)nitroaethan
• 英文别名: 1-(2,4-dichlorophenyl)-2-nitroethane；2,4-dichloro-1-(2-nitroethyl)benzene
• CAS: 72538-34-2
• 化学式: C₈H₇Cl₂NO₂
• 分子量: 220.055
• InChiKey: RCXBYHOGBFAQEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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：

  2-(2,4-Dichlorphenyl)nitroaethan 、 4-氯苯甲醛 在 potassium fluoride 、 盐酸二甲胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以20%的产率得到1-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-2-nitro-1-propene
  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：

  2,4-二氯苯甲醛 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 2-(2,4-Dichlorphenyl)nitroaethan
  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

• The highly chemoselective transfer hydrogenation of the carbon–carbon double bond of conjugated nitroalkenes by a rhodium complex
  作者：Jing Xiang、Er-Xiao Sun、Chun-Xia Lian、Wei-Cheng Yuan、Jin Zhu、Qiwei Wang、Jingen Deng

  DOI：10.1016/j.tet.2012.04.028

  日期：2012.6

  Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp∗]2–diamine complex (Cp∗=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl-isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction

  通过[催化的RhCl缀合的硝基烯烃化学选择性转移氢化2的Cp * ] 2 -二胺复合物（CP * =η 5 -C 5我5）使用HCOOH / ET 3 N（5：2）（TEAF）作为氢源，实现。各种硝基苯乙烯，β-甲基硝基苯乙烯和3-甲基-4-硝基-5-链烯基-异恶唑均能在短时间内以良好或极好的收率顺利还原。在反应条件下，其他官能团是惰性的。
• A Multicomponent Reaction between α-Substituted Acroleins, Nitroalkanes and Paraformaldehyde: Efficient Construction of Nitro δ-Lactol
  作者：Fanglin Zhang、Yuefa Gong、Guoxi Xiong、Mohui Wei、Yirong Zhou、Yungui Li

  DOI：10.1055/s-0030-1260194

  日期：2011.11

  cascade reaction between α-substituted acroleins, nitroalkanes, and paraformaldehyde that proceeded smoothly to give high yields of functionalized δ-lactols under mild conditions, is described. This methodology is useful in the development of a concise synthetic route to natural products (±)-manzacidin A and C. multicomponent reaction - α-substituted acroleins - 1,8-diazabicyclo[5.4.0]undec-7-ene - δ-lactols

  描述了在温和的条件下，α-取代的丙烯醛，硝基烷和多聚甲醛之间的碱催化多组分级联反应，该反应平稳进行，可得到高产率的官能化δ-内酯。此方法可用于开发从简明的合成路线到天然产物（±）-山梨酸A和C的方法。 多组分反应-α-取代的丙烯醛-1,8-二氮杂双环[5.4.0]十一碳-7-烯-δ-内酯
• S-Benzyl isothiouronium chloride as a recoverable organocatalyst for the reduction of conjugated nitroalkenes with Hantzsch ester
  作者：Quynh Pham Bao Nguyen、Jae Nyoung Kim、Taek Hyeon Kim

  DOI：10.1016/j.tet.2012.05.104

  日期：2012.8

  The reduction of conjugated nitroalkenes into nitroalkanes with Hantzsch ester using S-benzyl isothiouronium chloride as a recoverable organocatalyst was successfully accomplished with high yield and excellent chemoselectivity.

  以S-苄基异硫脲鎓氯化物为可回收的有机催化剂，成功地完成了用汉茨（Hantzsch）酯将共轭硝基链烷还原为硝基链烷的反应。
• Carbon-alkylation of simple nitronate anions
  作者：Alan R. Katritzky、George de Ville、Ranjan C. Patel

  DOI：10.1039/c3979000602a

  日期：——

  Aliphatic nitro-compounds are α-alkylated in good yields by 1-substituted-2,4,6-triphenylpyridinium cations.

  脂肪族硝基化合物被1-取代的2,4,6-三苯基吡啶鎓阳离子高产率地进行α-烷基化。
• Reduction of α,β-unsaturated nitroolefins into nitroalkanes with Hantzsch ester promoted by isothiouronium salts
  作者：Sungmin Kang、Haney Lee、Taek Hyeon Kim

  DOI：10.1080/00397911.2019.1614627

  日期：2019.10.2

  Abstract α,β-Unsaturated nitroolefins were reduced into nitroalkanes with a Hantzsch ester, promoted by S-benzyl isothiouronium iodide. The reactions proceeded successfully to afford the desired products in high yields and with excellent chemoselectivity. Graphical Abstract

  摘要 在 S-苄基异硫脲碘化物的促进下，α,β-不饱和硝基烯烃被 Hantzsch 酯还原成硝基烷烃。反应成功进行，以高产率和优异的化学选择性提供所需的产物。图形概要