(E)-ethyl 2-(2-(4-chlorophenyl)hydrazono)propanoate | 91473-66-4

• 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: (E)-ethyl 2-(2-(4-chlorophenyl)hydrazono)propanoate
• 英文别名: (E)-ethyl 2-(p-chlorophenylhydrazono)propanoate；ethyl 2-[(4-chlorophenyl)hydrazono]propionate；ethyl (2E)-2-[(4-chlorophenyl)hydrazono]propanoate；ethyl (2E)-2-[(4-chlorophenyl)hydrazinylidene]propanoate
• CAS: 91473-66-4
• 化学式: C₁₁H₁₃ClN₂O₂
• 分子量: 240.689
• InChiKey: TZUIRWBUCNJLAC-MDWZMJQESA-N

物化性质

• 熔点：
  137.5-138.5 °C
• 沸点：
  323.6±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(2-(4-chlorophenyl)hydrazono)propanoate 以37%的产率得到
  参考文献：
  名称：

  ISHIBASHI, FUMIHIDE;NASHIMA, TAKEO;NISHINO, JUNKO;KOBAYASHI, IKUKO;ICHIHA+, BULL. CHEM. SOC. JAP., 1986, 59, N 1, 73-76

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯胺 在 盐酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (E)-ethyl 2-(2-(4-chlorophenyl)hydrazono)propanoate
  参考文献：
  名称：

  Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives in vitro

  摘要：

  A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 x 10(3)- and 2.0 x 10(3)- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 mu M), respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.055

文献信息

• Geometrical Isomerism of Phenylhydrazones of α-Keto Esters. II.<i>p</i>-Substituted Phenylhydrazones of Ethyl Pyruvate and 2,4-Dinitrophenylhydrazones of Some α-Keto Esters
  作者：Fumihide Ishibashi、Takeo Nashima、Junko Nishino、Ikuko Kobayashi、Yoshinori Ichihara、Yoshimi Kitagawa、Shigeko Sasaki、Masako Yoshikawa、Atsuko Matsuoka、Keiko Yamamoto

  DOI：10.1246/bcsj.59.73

  日期：1986.1

  molecule on the basis of IR and 1H NMR spectra. In all cases, isomers with higher Rf-values on a silica gel TLC (using benzene as a developing solvent) involved an intramolecular hydrogen bonding between the imino hydrogen and the ester carbonyl oxygen. Thus, the Z-structure was assigned. An E-structure was assigned to other isomers with lower Rf-values. The present assignment is, thus, entirely the same

  丙酮酸乙酯的各种取代苯腙和一些α-酮酯的2,4-二硝基苯腙的每种几何异构体均以纯态分离。通过将腙在含有 C、H 和 Cl 的有机溶剂中的溶液保持在黑暗中，使前腙的 E-异构体部分异构化为 Z-异构体。根据 IR 和 1H NMR 光谱，每个分子都具有 E 或 Z 结构。在所有情况下，在硅胶 TLC（使用苯作为展开溶剂）上具有较高 Rf 值的异构体涉及亚氨基氢和酯羰基氧之间的分子内氢键。因此，指定了 Z 结构。E 结构被分配给具有较低 Rf 值的其他异构体。因此，目前的分配与先前调查中提出的分配完全相同。
• N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor
  作者：Jason G. Kettle、Alan W. Faull、Andy J. Barker、D.Huw Davies、Michael A. Stone

  DOI：10.1016/j.bmcl.2003.10.049

  日期：2004.1

  Screening of the corporate database led to the discovery of a novel series of N-benzylindole-2-carboxylic acid CCR2b chemokine receptor antagonists. These compounds demonstrate high affinity and functional inhibition of the CCR2b receptor. A discussion of the structure-activity relationships is presented, together with evidence for a highly selective receptor binding profile. (C) 2003 Elsevier Ltd. All rights reserved.
• Molecular design of pyrazolo[3,4-d]pyridazines
  作者：V. S. Matiichuk、M. A. Potopnyk、N. D. Obushak

  DOI：10.1134/s1070428008090182

  日期：2008.9

  Reactions of arenediazonium chlorides with ethyl 2-methyl-and 2-chloro-4-oxobutanoates gave, respectively, ethyl 2-(arylhydrazono)propanoates and chloro(arylhydrazono)acetates. Ethyl 2-(arylhydrazono)-propanoates reacted with the Vilsmeier-Haak reagent to give ethyl 1-aryl-4-formyl-1H-pyrazole-3-carboxylates. Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates were obtained by reaction of chloro(arylhydrazono) acetates with acetylacetone. Reactions of the obtained pyrazole derivatives with hydrazine and methylhydrazine led to the formation of the corresponding 3,4-R(2)(1)-6-R(2)-2-aryl-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-ones (R(1), R(2) = H, Me) which were subjected to alkylation and sulfurization.
• Murakami, Yasuoki; Yokoyama, Yuusaku; Miura, Tomoko, Heterocycles, 1984, vol. 22, # 5, p. 1211 - 1216
  作者：Murakami, Yasuoki、Yokoyama, Yuusaku、Miura, Tomoko、Hirasawa, Hiroko、Kamimura, Yuuko、Izaki, Miyako

  DOI：——

  日期：——
• VLAD L. A.; KORPAN A. I.; ZHUNGIETU G. I., BUL. AKAD. SHTIINTSE RSSMOLD., IZV. AN MOLDSSR. CEP. BIOL. I XIM. N., 197+
  作者：VLAD L. A.、 KORPAN A. I.、 ZHUNGIETU G. I.

  DOI：——

  日期：——