2-[Acetoxy-(2-chloro-5-nitro-phenyl)-methyl]-acrylic acid methyl ester | 845866-29-7

• 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-[Acetoxy-(2-chloro-5-nitro-phenyl)-methyl]-acrylic acid methyl ester
• 英文别名: Methyl 2-[acetyloxy-(2-chloro-5-nitrophenyl)methyl]prop-2-enoate
• CAS: 845866-29-7
• 化学式: C₁₃H₁₂ClNO₆
• 分子量: 313.694
• InChiKey: JZTGDGXOFWPBEG-UHFFFAOYSA-N

物化性质

• 沸点：
  431.7±45.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[Acetoxy-(2-chloro-5-nitro-phenyl)-methyl]-acrylic acid methyl ester 在 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70%的产率得到methyl 6-nitro-2-hydroxyimino-2H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman­ Acetates and Conversion into Several Coumarin Derivatives

  摘要：

  描述了一种从相应的Baylis-Hillman醋酸盐中快速简便地获得甲基（E）-2-硝基甲基肉桂酸酯的方法，该方法使用NaNO2在DMF中进行。一些邻氯-2-硝基甲基肉桂酸酯经历分子内芳香取代反应，随后重排生成香豆素衍生物。

  DOI：

  10.1055/s-2004-834916
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 在 三乙烯二胺 作用下， 生成 2-[Acetoxy-(2-chloro-5-nitro-phenyl)-methyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Methyl (E)-2-Nitromethylcinnamates Derived from Baylis-Hillman­ Acetates and Conversion into Several Coumarin Derivatives

  摘要：

  描述了一种从相应的Baylis-Hillman醋酸盐中快速简便地获得甲基（E）-2-硝基甲基肉桂酸酯的方法，该方法使用NaNO2在DMF中进行。一些邻氯-2-硝基甲基肉桂酸酯经历分子内芳香取代反应，随后重排生成香豆素衍生物。

  DOI：

  10.1055/s-2004-834916

文献信息

• One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita–Baylis–Hillman reaction as a key step
  作者：Hae-Won Yang、Ji-Su Choi、Sang-Jin Lee、Byung-Woo Yoo、Cheol Min Yoon

  DOI：10.1080/17415993.2015.1124275

  日期：2016.3.3

  efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of (Z)-S-2-alkoxycarbonyl-3-acylallyl ethanethioates and (E)-S-2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonitrile) was developed. Our method consisted of Morita–Baylis–Hillman reaction of benzaldehydes and activated alkenes using DABCO followed by acetylation using

  从苯甲醛和活化烯烃（甲基）合成 (Z)-S-2-alkoxycarbonyl-3-acylallyl 乙硫酸酯和 (E)-S-2-cyano-3-acylallyl 乙硫酸酯的有效、区域选择性和立体选择性一锅法丙烯酸酯和丙烯腈）。我们的方法包括苯甲醛和活化烯烃使用 DABCO 的 Morita-Baylis-Hillman 反应，然后使用乙酸酐和催化量的 DMAP 乙酰化，以及 SN2' 与 DMF 中硫代乙酸钾的反应。前两个反应在无溶剂条件下进行。图形概要
• Reactive Pt(II) center as part of redox-active quinoline-based heterocyclic scaffolds toward new anticancer leads
  作者：Sateeshkumar Kumbhakonam、Soumya Saroj、Nalini Venkatesan、Karunagaran Devarajan、Muraleedharan K. Manheri

  DOI：10.1016/j.bmcl.2020.127594

  日期：2020.11

  New cisplatin analogs in which the diamminedichloro-Pt(II) unit is conjugated to dihydroquinoline- or tetrahydroquinoline frameworks were synthesized and subjected to biological evaluation in order to understand their effects on cellular redox homeostasis and cell viability. They exhibited better selectivity towards cancer cells (A549) compared to mice fibroblast NIH3T3 cells, with cytotoxicity in

  合成了新的顺铂类似物，其中将二氨二氯-Pt（II）单元与二氢喹啉或四氢喹啉骨架结合，并进行了生物学评估，以了解它们对细胞氧化还原稳态和细胞活力的影响。与小鼠成纤维细胞NIH3T3细胞相比，它们对癌细胞（A549）表现出更好的选择性，其细胞毒性与顺铂相同。ROS水平存在结构依赖性变化，并且还能够诱导细胞死亡，这由亚G1期细胞的积累证明。
• Myeong, Jong Cha; Young, Seok Song; Han, Eun-Gu, Journal of Heterocyclic Chemistry, 2008, vol. 45, # 1, p. 235 - 240
  作者：Myeong, Jong Cha、Young, Seok Song、Han, Eun-Gu、Lee, Kee-Jung

  DOI：——

  日期：——
• FtsZ inhibition and redox modulation with one chemical scaffold: Potential use of dihydroquinolines against mycobacteria
  作者：Sridevi Duggirala、John Victor Napoleon、Rakesh P. Nankar、V. Senu Adeeba、Muraleedharan K. Manheri、Mukesh Doble

  DOI：10.1016/j.ejmech.2016.07.058

  日期：2016.11

  The dual effect of FtsZ inhibition and oxidative stress by a group of 1,2-dihydroquinolines that culminate in bactericidal effect on mycobacterium strains is demonstrated. They inhibited the non-pathogenic Mycobacterium smegmatis mc(2) 155 with MIC as low as 0.9 mu g/mL and induced filamentation. Detailed studies revealed their ability to inhibit polymerization and GTPase activity of MtbFtsZ (Mycobacterial filamentous temperature sensitive Z) with an IC50 value of similar to 40 mu M. In addition to such target specific effects, these compounds exerted a global cellular effect by causing redox-imbalance that was evident from overproduction of ROS in treated cells. Such multi-targeting effect with one chemical scaffold has considerable significance in this era of emerging drug resistance and could offer promise in the development of new therapeutic agents against tuberculosis. (C) 2016 Elsevier Masson SAS. All rights reserved.