ethyl (E)-2-(2-(2-chlorophenyl)hydrazono)propanoate | 43142-70-7

• 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: ethyl (E)-2-(2-(2-chlorophenyl)hydrazono)propanoate
• 英文别名: 2-(2-chloro-phenylhydrazono)-propionic acid ethyl ester；2-(2-Chlor-phenylhydrazono)-propionsaeure-aethylester；Brenztraubensaeureaethylester-(2-chlor-phenylhydrazon)；(E)-Ethyl-pyruvat-2-chlorphenylhydrazon；Propanoic acid, 2-(2-chlorophenylhydrazono)-, ethyl ester；ethyl (2E)-2-[(2-chlorophenyl)hydrazinylidene]propanoate
• CAS: 43142-70-7
• 化学式: C₁₁H₁₃ClN₂O₂
• 分子量: 240.689
• InChiKey: HWZBVPRPFNROEW-MDWZMJQESA-N

物化性质

• 沸点：
  319.5±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)：
  3.2
• 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：

  ethyl (E)-2-(2-(2-chlorophenyl)hydrazono)propanoate 在 喹啉 、 氢氧化钾 、 PPA 、 copper oxide-chromium oxide 作用下， 生成 7-氯吲哚
  参考文献：
  名称：

  Bz取代的吲哚和色氨酸合成实验。第三部分 四个Bz-氯吲哚和-色氨酸的合成

  摘要：

  DOI：

  10.1039/jr9550003499
• 作为产物：
  描述：

  丙酮酸乙酯 、 2-氯苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以50%的产率得到ethyl (E)-2-(2-(2-chlorophenyl)hydrazono)propanoate
  参考文献：
  名称：

  3取代的1H-吲哚-2-羧酸衍生物作为一类新的CysLT1选择性拮抗剂的发现。

  摘要：

  吲哚衍生物3-（（E）-3-（（3-（（E）-2-（7-氯喹啉-2基）乙烯基）苯基）氨基）-3-氧代丙-1-烯-1-基） -7-甲氧基-1H-吲哚-2-羧酸（17k）被确定为一种新型且高效的选择性CysLT1拮抗剂，CysLT1和CysLT2的IC50值为0.0059 +/- 0.0011和15 +/- 4μM，分别。

  DOI：

  10.1021/acsmedchemlett.5b00482

文献信息

• Fischer Indolization of Variously ortho-Substituted Phenylhydrazones. Fischer Indolization and Its Related Compounds. XXV.
  作者：Yasuoki MURAKAMI、Toshiko WATANABE、Yuusaku YOKOYAMA、Junko NAOMACHI、Haruo IWASE、Noriko WATANABE、Michiyo MORIHATA、Naomi OKUYAMA、Hiroyuki KAMAKURA、Tomoko TAKAHASHI、Hideko ATODA、Toshiaki TOJO、Kenji MORITA、Hisashi ISHII

  DOI：10.1248/cpb.41.1910

  日期：——

  Various kinds of ethyl pyruvate 2-(2-substituted phenyl)hydrazones (1) were subjected to Fischer indolization with acid catalysts. All the phenylhydrazones gave corresponding normal 7-substituted indoles (2). In addition, phenyl-hydrazones whose ortho-substituent is electron-donative or has a central atom with an unshared electron pair tended to give the 4- or 5-substituted indole (3), which was produced by migration of the ortho-substituent during cyclization, whereas those whose ortho-substituent is electron-attractive tended to give little or no such abnormal product. The kind of acid catalyst used had some effect on the yield ratio of products but not on the kind of products.

  各种丙酮酸乙酯 2-（2-取代苯基）酰肼（1）在酸催化剂作用下进行费歇尔吲哚化反应。所有的苯肼都得到了相应的 7-取代吲哚（2）。此外，如果苯肼的正位取代基是电子疏导型的，或者其中心原子上有一个未共享的电子对，则往往会产生 4 或 5 取代的吲哚（3），这是由正位取代基在环化过程中发生迁移而产生的；而如果苯肼的正位取代基是电子吸引型的，则往往很少或根本不会产生这种异常产物。所使用的酸催化剂对产物的产率有一定影响，但对产物的种类没有影响。
• Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists
  作者：Gay P. Fagan、Christopher B. Chapleo、Anthony C. Lane、Malcolm Myers、Alan G. Roach、Colin F. C. Smith、Michael R. Stillings、Anthony P. Welbourn

  DOI：10.1021/jm00400a009

  日期：1988.5

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.
• Hewitt, Journal of the Chemical Society, 1893, vol. 63, p. 871
  作者：Hewitt

  DOI：——

  日期：——
• 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.
• 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：——

表征谱图