2-methyl-1,2-dihydro-3H-indol-3-one | 53903-96-1

• 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: 2-methyl-1,2-dihydro-3H-indol-3-one
• 英文别名: 2-methyl-3-indolinone；2-methylindolin-3-one；2-methyl-1,2-dihydroindol-3-one
• CAS: 53903-96-1
• 化学式: C₉H₉NO
• mdl: MFCD19219372
• 分子量: 147.177
• InChiKey: KVGKFRJNCLJWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1,2-dihydro-3H-indol-3-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-甲基二氢吲哚-3-酮肟
  参考文献：
  名称：

  Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process

  摘要：

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.

  DOI：

  10.1021/acs.joc.6b02774
• 作为产物：
  描述：

  2-甲基吲哚 在 air 、 cadmium(II) sulphide 作用下， 以 水 为溶剂， 反应 0.25h， 生成 2-methyl-1,2-dihydro-3H-indol-3-one 、 N-(2-甲酰基苯基)乙酰胺
  参考文献：
  名称：

  Colloidal CdS-induced photocatalytic reaction of 2-methylindole?mechanistic analysis of oxidation of indoles

  摘要：

  2-Methylindole (2-MI) is adsorbed on the surface of colloidal CdS particles with an adsorption intensity of 0.6 x 10(3) dm(3) mol(-1). A new emission band at 530 nm is produced by forming an exciplex between excited CdS and 2-MI and the red emission due to CdS is simultaneously quenched. The emission maxima of green bands for different indoles increase in the order indole < tryptophan < 2-MI < 3-MI and are observed at 508, 520, 530 and 540 nm, respectively. The shift in emission maxima is related to the oxidation potential of these substrates. The irradiation of an aerated reaction mixture containing CdS and 2-MI with visible light induces the oxidation of adsorbed 2-MI by photogenerated holes to produce 2-methyl-3-indolinone and 2-acetamidobenzaldehyde. The latter product is formed due to oxidative C-C bond cleavage of the pyrrole ring. The reactivity of trapped holes towards the adsorbed 2-MI is evidenced by a decrease in the lifetime of the red emission of CdS in the presence of 2-MI. In this reaction the possibility of the participation of singlet oxygen is ruled out. A general mechanism of CdS-induced oxidation of indoles is discussed. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199804)11:4<277::aid-poc3>3.0.co;2-t

文献信息

• A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C
  作者：Fan Xu、Myles W. Smith

  DOI：10.1039/d1sc03533a

  日期：——

  The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls via nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps)

  吲哚酚单元是生物碱天然产物和生物活性化合物中常见的结构基序。在这里，我们报告了一种通用方法，通过与 2-烷氧基吲哚酚中间体的亲核试剂偶联，将容易获得的 2-取代吲哚转化为 2,2-二取代吲哚酚，并展示其在生物碱 brevianamide A（7 个步骤）和 trigonoliimine 的简短全合成中的实用性C（6 个步骤）。所开发的方法操作简单，并且在亲核体特性和吲哚取代方面表现出广泛的范围，容忍 2-烷基取代基和游离吲哚 N-H 基团，这些元素超出了大多数现有方法的范围。螺环吲哚酚产物也可以通过分子内亲核捕获来获得。
• [EN] QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES UTILES EN TANT QU'INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2007117778A9

  公开（公告）日：2009-05-22
• Synthesis of <i>N</i>-Aryl Oxindole Nitrones through a Metal-Free Selective <i>N</i>-Arylation Process
  作者：Si-Yi Wu、Xiao-Pan Ma、Cui Liang、Dong-Liang Mo

  DOI：10.1021/acs.joc.6b02774

  日期：2017.3.17

  An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.
• Colloidal CdS-induced photocatalytic reaction of 2-methylindole?mechanistic analysis of oxidation of indoles
  作者：Anil Kumar、Sanjay Kumar

  DOI：10.1002/(sici)1099-1395(199804)11:4<277::aid-poc3>3.0.co;2-t

  日期：1998.4

  2-Methylindole (2-MI) is adsorbed on the surface of colloidal CdS particles with an adsorption intensity of 0.6 x 10(3) dm(3) mol(-1). A new emission band at 530 nm is produced by forming an exciplex between excited CdS and 2-MI and the red emission due to CdS is simultaneously quenched. The emission maxima of green bands for different indoles increase in the order indole < tryptophan < 2-MI < 3-MI and are observed at 508, 520, 530 and 540 nm, respectively. The shift in emission maxima is related to the oxidation potential of these substrates. The irradiation of an aerated reaction mixture containing CdS and 2-MI with visible light induces the oxidation of adsorbed 2-MI by photogenerated holes to produce 2-methyl-3-indolinone and 2-acetamidobenzaldehyde. The latter product is formed due to oxidative C-C bond cleavage of the pyrrole ring. The reactivity of trapped holes towards the adsorbed 2-MI is evidenced by a decrease in the lifetime of the red emission of CdS in the presence of 2-MI. In this reaction the possibility of the participation of singlet oxygen is ruled out. A general mechanism of CdS-induced oxidation of indoles is discussed. (C) 1998 John Wiley & Sons, Ltd.