1-butylindolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-butylindolin-2-one
• 英文别名: Butyloxindole；1-butyl-3H-indol-2-one
• 化学式: C₁₂H₁₅NO
• mdl: MFCD06662361
• 分子量: 189.257
• InChiKey: ZBFPDJCCDKXTOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-butylindolin-2-one 在 mercury(II) oxide 、 碘 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 50.0h， 以72%的产率得到N-butyl-5-iodo-indolin-2-one
  参考文献：
  名称：

  Thiophene-functionalized octupolar triindoles: Synthesis and photophysical properties

  摘要：

  Two thiophene-functionalized octupolar triindole molecules were synthesized through Suzuki and Sonogashira cross-coupling reactions. Their photophysical and electrochemical properties were explored. The spectroscopic data demonstrate that triindole is an excellent rich electronic central donor for building octupolar optoelectronic molecules and possesses excellent luminescent properties. Thiophenylethynyl substituted triindole compound 3,8,13-tri(2-thiophenylethynyl)-5,10,15-tributyltriindole forms an intermolecular aggregation induced by pi-pi stacking from the rigid coplanar molecular scaffold. The redox curves and results of theoretical calculation imply that the two compounds have low ionization potential and low E-1/2 (oxd) which may be originated from the high electronic density of both triindole and thiophene groups. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.08.008
• 作为产物：
  描述：

  邻溴苯乙酸 在 氯化亚砜 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 11.0h， 生成 1-butylindolin-2-one
  参考文献：
  名称：

  邻溴苯乙酰胺的环化和氧化反应，用于合成羟吲哚和异靛蓝

  摘要：

  通过容易的KOH / DMSO促进邻溴苯基乙酰胺的分子内环化以良好的产率获得N-取代的羟吲哚。此外，在乙酸铜（II）一水合物，碘代苯二乙酸盐和KOH / DMSO的存在下，通过依次的邻溴苯基乙酰胺的分子内环化，氧化和缩合，可以容易地合成异靛蓝衍生物。该方法使用邻-溴苯基乙酰胺作为唯一原料，可以方便地合成一系列羟吲哚和对称的生物学上重要的（E）-双吲哚-2-酮。根据对照实验结果阐明了反应机理。

  DOI：

  10.1016/j.tet.2017.12.005

文献信息

• Acylation of oxindoles using methyl/phenyl esters <i>via</i> the mixed Claisen condensation – an access to 3-alkylideneoxindoles
  作者：Ramdas Sreedharan、Purushothaman Rajeshwaran、Pradeep Kumar Reddy Panyam、Saurabh Yadav、C. M. Nagaraja、Thirumanavelan Gandhi

  DOI：10.1039/d0ob00789g

  日期：——

  Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources, viz. methyl and phenyl esters, which acylate oxindoles via the mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of

  在酰化过程中，主要使用侵蚀性的酰氯和化学计量的偶联剂来合成羰基束缚的杂环。在这里，我们报告简单的酰基来源，即。甲酯和苯酯，它们通过混合的克莱森缩合反应酰化吲哚。这种简单的方法是由LiHMDS和KOtBu介导的，并成功地应用于各种基材。这是一个值得注意的转变，它跳过了烯醇化物和酰化的逐步生成，并且该反应在中等温度下进行，没有任何副反应。该方案产生了芳基环中的邻位取代基的第一个例子，该芳基环上有供电子和吸电子底物。有趣的是，坚固的有机金属二茂铁基甲基酯在这些条件下容易裂解。此外，
• Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
  作者：Pradeep Kumar Reddy Panyam、Bharat Ugale、Thirumanavelan Gandhi

  DOI：10.1021/acs.joc.8b00264

  日期：2018.8.3

  designed fluorene-based mono- and bimetallic Pd–PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

  合成了合理设计的基于芴的单金属和双金属Pd-PEPPSI配合物，并证明了对一锅顺序的吲哚α-芳基化/烷基化反应有效。这种简化的方法可在温和的反应条件下以优异的收率（高达89％）有效地获得官能化的3,3-二取代的羟吲哚。
• Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon–carbon double bond formation
  作者：Zhi-Yu Tan、Ke-Xin Wu、Lu-Shan Huang、Run-Shi Wu、Zheng-Yu Du、Da-Zhen Xu

  DOI：10.1039/c9gc03639c

  日期：——

  The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)–H/C(sp3)–H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations

  描述了铁催化的C（sp 3）–H / C（sp 3）–H键的交叉脱氢偶联（CDC），可通过4H消除得到烯烃。该方法使用空气（分子氧）作为理想的氧化剂，并且在温和，无配体和无碱的条件下进行。H 2 O是唯一的副产物。还获得了对官能团的良好耐受性和高产率。初步的机械研究表明，目前的转变涉及一个根本过程。
• Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles
  作者：Rajamohan R. Poondra、Nicholas J. Turner

  DOI：10.1021/ol0473804

  日期：2005.3.1

  two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide. [structure: see text]

  已经开发了用于合成N-取代的羟吲哚的通用方法。此两步过程涉及在2-卤代芳酸与各种烷基胺和苯胺之间首先形成微波辅助的酰胺键，然后在水性条件下进行钯催化的分子内酰胺化反应。在烷基胺的情况下，该过程可以一锅法进行，而无需分离中间体酰胺。[结构：见文字]
• Copper powder-catalyzed chelation-assisted cascade reaction of o-chloroarylacetic acids with amines under solvent- and ligand-free conditions: synthesis of oxindoles
  作者：Jiang-Sheng Li、Guo-Qin Chen、Qian Yang、Zhi-Wei Li、Ci-Zhi Liu、Peng-Mian Huang

  DOI：10.1039/c7ra08123e

  日期：——

  An efficient method to construct oxindole scaffolds from o-chloroarylacetic acids/esters with amines has been explored. This cascade protocol involves the in situ generation of o-aminoarylacetic acid derivatives by the copper powder catalyzed and weak O-chelation assisted Ullmann amination of unactivated C–Cl bonds under air, and solvent-/ligand-free conditions followed by annulative N-acylation.

  已经探索了由邻氯代乙酸/酯与胺一起构建羟吲哚骨架的有效方法。该级联方案涉及在空气中，在无溶剂/无配体的条件下，通过铜粉催化的铜粉催化和弱O-螯合辅助未激活的C-Cl键的Ullmann胺化原位生成邻氨基芳酸衍生物，然后进行环化N-酰化。