3-(4-chloro-phenylimino)-5-nitro-1,3-dihydro-indol-2-one | 57743-31-4

• 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-nitro-1,3-dihydro-indol-2-one
• 英文别名: 5-nitro-3-(4-chloroimino)-indolin-2-one；3-(4-chlorophenyl)imino-5-nitro-1H-indol-2-one
• CAS: 57743-31-4
• 化学式: C₁₄H₈ClN₃O₃
• 分子量: 301.689
• InChiKey: NVQGNGYMZDSZHK-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C(Solv: ethanol (64-17-5))
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-phenylimino)-5-nitro-1,3-dihydro-indol-2-one 、 硫代乳酸 以 甲苯 为溶剂， 反应 10.0h， 以38%的产率得到5-nitro-3'-(4-chlorophenyl)-5'-methyl-spiro[3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione
  参考文献：
  名称：

  潜在的抗惊厥药。七。5'-甲基螺[3 H-吲哚-3,2'-噻唑烷] -2,4'（1 H）-二酮的合成

  摘要：

  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。

  DOI：

  10.1002/jhet.5570210203
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 生成 3-(4-chloro-phenylimino)-5-nitro-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

• Synthesis and Antibacterial Activity of Some 5-Nitro-3-phenyliminoindol-2(3H)-ones and Their N-Mannich Bases
  作者：Roy W. Daisley、Vasanti K. Shah

  DOI：10.1002/jps.2600730333

  日期：1984.3

  The antimicrobial and antifungal activities of a series of 5-nitro-3-phenyliminoindol-2(3H)-ones and their 1-piperidinomethyl analogues (N-Mannich bases) were investigated. Growth inhibition of Gram-positive bacteria was observed with little or no activity against Gram-negative bacteria. Antifungal activity was absent. The syntheses were accomplished from 5-nitroindol-2,3-dione by condensation with

  研究了一系列5-硝基-3-苯基亚氨基吲哚-2（3H）-及其1-哌啶子基甲基类似物（N-曼尼希碱）的抗微生物和抗真菌活性。观察到革兰氏阳性细菌的生长抑制几乎没有或没有针对革兰氏阴性细菌的活性。没有抗真菌活性。通过与适当的苯胺缩合，然后形成N-曼尼希碱，由5-硝基吲哚-2，3-二酮完成合成。
• 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.
• DAISLEY, R. W.;SHAH, VASANTI, K., J. PHARM. SCI., 1984, 73, N 3, 407-408
  作者：DAISLEY, R. W.、SHAH, VASANTI, K.

  DOI：——

  日期：——
• RAJOPADHYE, M.;POPP, F. D., J. HETEROCYCL. CHEM., 1984, 21, N 2, 289-291
  作者：RAJOPADHYE, M.、POPP, F. D.

  DOI：——

  日期：——