3-(4-chloro-phenylimino)-5-methyl-1,3-dihydro-indol-2-one | 61294-08-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-chloro-phenylimino)-5-methyl-1,3-dihydro-indol-2-one
• 英文别名: 3-(4-Chloroanilino)-5-methylindol-2-one；3-(4-chlorophenyl)imino-5-methyl-1H-indol-2-one
• CAS: 61294-08-4
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: XQBSLLAUGJLGHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-phenylimino)-5-methyl-1,3-dihydro-indol-2-one 以 乙醇 为溶剂， 反应 6.17h， 生成 N-(4-bromophenyl)-2-(5-methyl-2-oxo-1-(piperidin-1-ylmethyl)indolin-3-ylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Varma, Rajendra S.; Pandey, Rajnish K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 2, p. 157 - 159

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxyimino-N-p-tolyl-acetamide 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 3-(4-chloro-phenylimino)-5-methyl-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Sridhar; Ramesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 668 - 672

  摘要：

  DOI：

文献信息

• Potential anticonvulsants. VII. Synthesis of 5′-methylspiro[3<i>H</i>-indole-3,2′-thiazolidine]-2,4′(1<i>H</i>)-diones
  作者：Milind Rajopadhye、Frank D. Popp

  DOI：10.1002/jhet.5570210203

  日期：1984.3

  The title compounds have been prepared, by the cyclocondensation of thiolactic acid with isatin-3-imines. 5′-Methyl-3′-phenyl-spiro[3H-indole-3,2′-thiazolidine]-2,4′(1H)-dione has been subjected to the Mannich condensation to give 1-substituted derivatives. With one exception, all of the products were inactive in an anticonvulsant screen.

  标题化合物是通过巯基乳酸与Isatin-3-imines的环缩合反应制得的。将5'-甲基-3'-苯基-螺基[3 H-吲哚-3,2'-噻唑烷] -2,4'（1 H）-二酮进行曼尼希缩合，得到1-取代的衍生物。除一个例外，所有产品在抗惊厥筛查中均处于非活性状态。
• Protecting-Group-Free Synthesis of 3-Amino-3-α-prenyl-oxindoles through the Direct Prenylation of Isatin-Derived Imines
  作者：De-Feng Li、Hai-Shan Jin、Jing-Ru Zhang、Yi-Xuan Jiang、Li-Ming Zhao

  DOI：10.1002/ejoc.201800881

  日期：2018.9.16

  A zinc‐mediated α‐selective prenylation of isatin‐derived imine in a sealed tube has been developed. The method is highly efficient and operationally simple with its use of readily available prenyl bromide as the prenyl source. The obtained prenylated adduct can be further manipulated to other more complicated derivatives through cyclization or oxidation.

  已开发出在密封管中由锌介导的α-伊斯丁衍生的亚胺选择性乙二烯基化。该方法通过使用容易获得的异戊烯基溴化物作为异戊二烯源来进行高效和操作简单。可以通过环化或氧化将所得的烯丙基化的加合物进一步操纵为其他更复杂的衍生物。
• Synthesis of 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3,5′-pyrroline]-2,3′-dione via one-pot reaction of arylamines, acetone, and isatins
  作者：Yan Sun、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.tetlet.2012.05.023

  日期：2012.7

  An efficient synthetic method for 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3,5′-pyrroline]-2,3′-diones was successfully developed via the one-pot domino reaction of arylamines, acetone, and isatins in acetic acid. The reaction mechanism involved the sequential Michael addition and ring closure of the in situ formed 3-N-aryliminoisatin and isatylidene acetone.

  通过一锅多米诺反应成功开发了一种有效的合成方法，用于合成1'-芳基-2'-（2-氧吲哚-3-基）螺[吲哚啉-3,5'-吡咯啉] -2,3'-二酮乙酸中的芳基胺，丙酮和靛红。该反应机理涉及依次形成原位形成的3- N-芳基芥子素和异亚丙基丙酮的迈克尔加成和闭环。
• IMPROVED ONE-POT SYNTHESIS OF 3-SPIRO INDOLINES UNDER MICROWAVE IRRADIATION
  作者：Anshu Dandia、Mitali Saha、Harshita Taneja

  DOI：10.1080/10426509808035679

  日期：1998.8.1

  The potential of the domestic microwave oven has been utilized to accelerate the one-pot synthesis of spiro[indole-thiazolidine]diones and spiro[indole-benzothiazine]diones by condensation of substituted indole-2,3-diones (1) and appropriate anilines (2) with mercaptopropionic acid (4a/b) and o-mercaptobenzoic acid (5) in open borosilicate vessels, using ethanol as energy transfer medium. The reaction rate was 400-500 times faster than the reaction rate in the conventional way. Excellent isolated yields with easier workup than classical heating were the main advantages observed.
• Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives
  作者：Seshaiah Krishnan Sridhar、Muniyandy Saravanan、Atmakuru Ramesh

  DOI：10.1016/s0223-5234(01)01255-7

  日期：2001.8

  Schiff bases and hydrazones of substituted isatins (1-28), were prepared by reacting isatin and aromatic primary amines/hydrazines. A new series of the corresponding N-Mannich base (29-35) was synthesised by reacting them with formaldehyde and diphenyl amine. The chemical structures were confirmed by means of H-1-NMR, IR spectral data and elemental analysis. The compounds were screened for antibacterial activity against seven Gram (+) and seven Gram (-) standard and pathological bacterial strains by the paper disc diffusion technique. The minimum inhibitory concentrations of the active compounds were determined. 1-Diphenyl amino-methyl-3-(4-bromo phenylimino)-1,3-dihydro-indol-3-one (30) and 3-(4-bromo phenylimino)-5-nitro-1,3-dihydroindol-3-one (13) were found to be the most actives compounds of the series. Mannich bases exhibited higher activity than the corresponding Schiff bases. (C) 2001 Editions scientifiques et medicales Elsevier SAS.