5-fluoro-1,3-dihydro-3-[(4-methoxyphenyl)imino]-2H-indole-2-one | 1326527-34-7

• 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: 5-fluoro-1,3-dihydro-3-[(4-methoxyphenyl)imino]-2H-indole-2-one
• 英文别名: 5-Fluoro-3-(4-methoxy-phenylimino)-1,3-dihydro-indol-2-one；5-fluoro-3-(4-methoxyphenyl)imino-1H-indol-2-one
• CAS: 1326527-34-7
• 化学式: C₁₅H₁₁FN₂O₂
• 分子量: 270.263
• InChiKey: YNBXJTVDBJNZSN-UHFFFAOYSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  5-fluoro-1,3-dihydro-3-[(4-methoxyphenyl)imino]-2H-indole-2-one 、 烯丙基三甲基硅烷 在 mercury (II) perchlorate trihydrate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到C₁₈H₁₇FN₂O₂
  参考文献：
  名称：

  A Hg(ClO₄)₂·3H₂O Catalyzed Sakurai–Hosomi Allylation of Isatins and Isatin Ketoimines Using Allyltrimethylsilane

  摘要：

  It is reported that Hg(ClO4)(2)center dot 3H(2)O could efficiently activate the cheap but less reactive allyltrimethylsilane for the allylation of isatins or isatin ketoimines, with catalyst loading down to 0.1 mol %. This is the first example of Sakurai-Hosomi allylation of ketoimines using allyltrimethylsilane. A rare example of chiral mercury catalysis is also reported.

  DOI：

  10.1021/ol202705g
• 作为产物：
  描述：

  5-氟靛红 、 甲氧苯胺 以 水 为溶剂， 反应 4.0h， 以96%的产率得到5-fluoro-1,3-dihydro-3-[(4-methoxyphenyl)imino]-2H-indole-2-one
  参考文献：
  名称：

  通过希夫碱“在水上”合成螺吲哚

  摘要：

  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 。

  DOI：

  10.1007/s00706-011-0697-x

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。
• 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。
• Rhodium-Catalyzed Asymmetric Formal Cycloadditions of Racemic Butadiene Monoxide with Imines
  作者：Zhaoqun Liu、Xiangqing Feng、Haifeng Du

  DOI：10.1021/ol301248d

  日期：2012.6.15

  sulfur−alkene hybrid ligand has proven to be highly effective for rhodium-catalyzed formal cycloaddition reactions of racemic butadiene monoxide and imines to furnish spirooxindole oxazolidines or 1,3-oxazolidines with high yields and stereoselectivities. A possible dynamic kinetic resolution as well as a kinetic resolution is considered to be involved in this catalytic process.

  一个简单的手性硫-烯烃杂合配体已被证明对于铑催化的外消旋丁二烯一氧化氮和亚胺的正式环加成反应具有很高的收率和立体选择性，从而可以提供螺氧并吲哚恶唑烷或1,3-恶唑烷。该催化过程涉及可能的动态动力学拆分以及动力学拆分。
• 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.