3-(4-methoxy-phenylimino)-5-methyl-1,3-dihydro-indol-2-one | 60283-77-4

• 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-methoxy-phenylimino)-5-methyl-1,3-dihydro-indol-2-one
• 英文别名: (3Z)-3-[(4-Methoxyphenyl)imino]-5-methyl-1,3-dihydro-2H-indol-2-one；3-(4-methoxyphenyl)imino-5-methyl-1H-indol-2-one
• CAS: 60283-77-4
• 化学式: C₁₆H₁₄N₂O₂
• mdl: MFCD01240174
• 分子量: 266.299
• InChiKey: KTQRVRPEWXKIPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxy-phenylimino)-5-methyl-1,3-dihydro-indol-2-one 、 硫代乳酸 以55%的产率得到
  参考文献：
  名称：

  RAJOPADHYE, MILIND;POPP, F. D., J. HETEROCYCL. CHEM., 24,(1987) N 6, 1637-1642

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基靛红 、 甲氧苯胺 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(4-methoxy-phenylimino)-5-methyl-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  咪唑基吡啶-In （OTf）3催化源自靛红的酮亚胺的对映选择性烯丙基化†

  摘要：

  描述了在咪唑基吡啶吡啶配体的存在下对衍生自靛红的酮亚胺的对映选择性In（OTf）3催化的烯丙基化。反应在温和条件下平稳进行，得到3-烯丙基3-氨基氧吲哚，具有良好的收率和中等至优异的对映选择性（至多97％ee）。

  DOI：

  10.1039/c6ob00551a

文献信息

• 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。
• “On water” synthesis of spiro-indoles via Schiff bases
  作者：Siva S. Panda、Subhash C. Jain

  DOI：10.1007/s00706-011-0697-x

  日期：2012.8

  AbstractA fast, efficient, and clean “on water” synthesis of new Schiff bases and their conversion to spiro compounds under microwave irradiation, as well as in water, is reported. Indol-2,3-diones were reacted separately with various heterocyclic and aromatic amines in water at room temperature to obtain corresponding Schiff bases in high purity and yield. These were then converted into corresponding

  摘要据报道，新的席夫碱快速，有效，清洁的“水上”合成以及在微波辐射下以及在水中均可将其转化为螺环化合物。吲哚-2，3-二酮在室温下分别与各种杂环胺和芳族胺反应，以高纯度和高收率获得相应的席夫碱。然后使用巯基乙酸在纯净条件下以及在回流下的水中在微波辐射下将它们转化为相应的螺环化合物。因此，开发了绿色合成方案以在生态友好的条件下合成新的分子，其轮廓得到改善，其中不形成废物或副产物。 图形概要 。
• A facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reaction
  作者：Yun-Lin Liu、Feng Zhou、Jun-Jie Cao、Cong-Bin Ji、Miao Ding、Jian Zhou

  DOI：10.1039/c0ob00174k

  日期：——

  The direct α-cyanoamination of isatins using TMSCN has been developed, which is carried out in methanol without any catalyst. A new bifunctional cinchona alkaloid-based phosphinamide catalyst 7 could promote the Strecker reaction of isatins derived ketimine with TMSCN in up to 74% ee.

  已开发出使用TMSCN直接对异靛酮进行α-氰胺化反应，该反应在无催化剂的情况下在甲醇中进行。一种新的基于奎宁生物碱的双功能磷酰胺催化剂7能够促进源自异靛酮的酮亚胺与TMSCN的斯特雷克反应，最高可达74%的对映体过剩。
• 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.
• Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro[imidazolidine-2-thione]bisoxindoles
  作者：Yan-Yan Han、Wen-Bing Chen、Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/ol203081x

  日期：2012.1.20

  An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.