(E)-ethyl 3-(4-chloro-3-nitrophenyl)acrylate | 42174-78-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-(4-chloro-3-nitrophenyl)acrylate
• 英文别名: ethyl 3-(4-chloro-3-nitrophenyl)acrylate；trans-ethyl 4-chloro 3-nitrocinnamate；ethyl (2E)-3-(4-chloro-3-nitrophenyl)acrylate；ethyl (E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate
• CAS: 42174-78-7
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: JWQUGIHGJKNZRN-GQCTYLIASA-N

物化性质

• 沸点：
  381.5±32.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(4-chloro-3-nitrophenyl)acrylate 在 盐酸 、 氨 、 氢气 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 25.0~100.0 ℃ 、275.79 kPa 条件下， 反应 51.0h， 生成
  参考文献：
  名称：

  新型二氢叶酸还原酶抑制剂的基于受体的设计：苯并咪唑和吲哚衍生物。

  摘要：

  尽管已经合成了数千种二氢叶酸还原酶（DHFR）抑制剂，但是所有非常有活性的化合物都是2,4-二氨基嘧啶或非常接近的类似物。本文介绍了2,4-二氨基-6-苄基苯并咪唑（3b）和相应的吲哚（4），以及更复杂的三环和四环衍生物（5和6）。这些是根据对大肠杆菌DHFR的已知X射线结构进行分子建模而设计的，目的是确定是否可以通过将一个氨基取代基置于5元含氮环中来彻底改变二氨基构型，第二个在稠环的邻位，并且仍然显着抑制DHFR。尽管电子角和键角与2,4-二氨基嘧啶的电子角和键角大不相同，pKa值在适当的范围内，并且氢键的距离看来是相当合理的。活性最高的化合物4非常不稳定，仅在10（-4）M范围内具有活性。通过建模研究，二氢茚并咪唑衍生物（如6）对酶显示出很好的拟合性，但活性较低。由于所制得的最具活性的化合物作为细菌DHFR的抑制剂比未取代的5-苄基-2,4-二氨基嘧啶弱2个数量级，因此我们得出这样的环

  DOI：

  10.1021/jm00108a022
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 4-氯-3-硝基苯甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到(E)-ethyl 3-(4-chloro-3-nitrophenyl)acrylate
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Leishmania N-Myristoyltransferase Inhibitors

  摘要：

  Inhibitors of Leishmania N-myristoyltransferase (NMT), a potential target for the treatment of leishmaniasis, obtained from a high-throughput screen, were resynthesized to validate activity. Crystal structures bound to Leishmania major NMT were obtained, and the active diastereoisomer of one of the inhibitors was identified. On the basis of structural insights, enzyme inhibition was increased 40-fold through hybridization of two distinct binding modes, resulting in novel, highly potent Leishmania donovani NMT inhibitors with good selectivity over the human enzyme.

  DOI：

  10.1021/jm5011397

文献信息

• Chromatography-Free Wittig Reactions Using a Bifunctional Polymeric Reagent
  作者：Peter Shu-Wai Leung、Yan Teng、Patrick H. Toy

  DOI：10.1021/ol1021614

  日期：2010.11.5

  The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after

  已经制备了带有两个不同试剂基团的聚苯乙烯的第一个例子。该膦和胺官能化的材料用于与醛和α-卤代酯，-酮或-酰胺的一锅法Wittig反应中。由于聚合物的非均质性质，仅在过滤和除去溶剂后，就可以以优异的收率以基本纯净的形式分离出这些反应的所需烯烃产物。
• Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions
  作者：Patrick Toy、Xuanshu Xia

  DOI：10.1055/s-0034-1380810

  日期：——

  rted triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene

  已经合成了聚乙烯亚胺负载的三苯基膦试剂，并在一系列单锅 Wittig 反应中用作高负载的双功能均质试剂，在简单的纯化程序后可提供高产率的所需产物。该方法还可以有效地用于串联反应序列，包括一锅 Wittig 反应，然后是新形成的烯烃产物的原位共轭还原。在这些转化中，维蒂希反应中产生的氧化膦基团作为催化剂在随后的还原反应中激活三氯硅烷。
• A Convenient Synthesis of Pyrrolo[3,4-<i>c</i>]quinolines
  作者：Miklós Nyerges、Andrea Virányi、Gábor Blaskó、László Tőke

  DOI：10.1055/s-2003-42425

  日期：——

  A new route to the pyrrolo[3,4-c]quinoline ring system has been developed. The synthesis proceeds stereoselectively in three steps, using 1,3-dipolar cycloaddition of azomethine ylides as a key step. First, a series of 4-arylpyrrolidine-3-carboxylic acids have been prepared from the appropriate cinnamic esters and a nonstabilized azomethine ylide. The reduction of a nitro group on the aromatic ring was followed by acid-catalyzed intramolecular lactam formation.

  一种新的合成吡咯并[3,4-c]喹啉环系的方法已经开发出来。该合成以立体选择性的方式进行，分为三步，采用了亚甲基亚胺酯的1,3-极性环加成反应作为关键步骤。首先，从适当的肉桂酸酯和一种非稳定的亚甲基亚胺酯合成了一系列4-芳基吡咯烷-3-羧酸。接下来对芳环上的硝基进行还原，然后经过酸催化的分子内内酰胺形成反应。
• Hapten Synthesis and Antibody Development for Polychlorinated Dibenzo-<i>p</i>-dioxin Immunoassays
  作者：James R. Sanborn、Shirley J. Gee、S. Douglass Gilman、Yukio Sugawara、A. Daniel Jones、Jane Rogers、Ferenc Szurdoki、Larry H. Stanker、Donald W. Stoutamire、Bruce D. Hammock

  DOI：10.1021/jf970716m

  日期：1998.6.1

  This paper reports the synthesis of haptens and the generation and preliminary evaluation of polyclonal antibodies for the detection of dioxins such as TCDD (2,3,7,8-tetrachlorodibenzo-p-dioxin) by ELISA (enzyme-linked immunosorbent assay). These novel haptens contain unsaturation between the halogenated dibenzo-p-dioxin ring system and the protein to which it is conjugated, presenting a rigid handle structure. The substitution pattern is identical with or similar to that of TCDD (i.e., 2,3,7,8- or 1,2,3,7,8-). Finally, the haptens lack polar groups for hydrogen bonding. In direct binding assays using the new polyclonal antibodies there was excellent recognition of hapten-protein conjugates, including recognition of those hapten conjugates that were not used as immunogens (i.e., assay systems heterologous in hapten structure). These haptens do elicit selective immune responses in rabbits. Their evaluation in an ELISA format demonstrated the usefulness of these haptens for the detection of dioxins. An IC50 of 0.8 ng/well (16 ng/mL) was observed for an unoptimized system that used 2,3,7-trichloro-8-methyldibenzo-p-dioxin as an analytical surrogate standard.