1-甲基-3-亚甲基-1,3-二氢-2H-吲哚-2-酮 | 59181-28-1

• 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
• 中文名称: 1-甲基-3-亚甲基-1,3-二氢-2H-吲哚-2-酮
• 英文名称: 1-methyl-3-methylene-1,3-dihydro-2H-indol-2-one
• 英文别名: 1-methyl-3-methyleneindolin-2-one；3-Methylenindolin-2-on；1-Methyl-3-methylideneindol-2-one
• CAS: 59181-28-1
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: XNZSWMJKDVOOBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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-甲基-3-亚甲基-1,3-二氢-2H-吲哚-2-酮 在 potassium acetate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 15.5h， 生成 2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)acetonitrile
  参考文献：
  名称：

  A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids

  摘要：

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.

  DOI：

  10.1021/ol200547m
• 作为产物：
  描述：

  N-(2-iodophenyl)-N-methylacrylamide 在 palladium diacetate potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1-甲基-3-亚甲基-1,3-二氢-2H-吲哚-2-酮
  参考文献：
  名称：

  Spiro-oxindoles via bimetallic [Pd(0)/Ag(I)] catalytic intramolecular Heck-1,3-dipolar cycloaddition cascade reactions

  摘要：

  The combination of an intramolecular Heck reaction with a subsequent Ag(l) catalysed imine --> azomethine ylide --> cycloaddition cascade is described for the formation of novel spiro-oxindoles. The reaction proceeds regiospecifically with good to excellent stereoselectivity and creates two new rings, three bonds and three stereocentres. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00331-3

文献信息

• Cyclocondensation of Amino-propargyl Silanes
  作者：Yizhong Wang、Joseph M. Ready

  DOI：10.1021/ol300724c

  日期：2012.5.4

  Amino-propargyl silanes condense with carbonyl compounds to form imines and subsequently cyclize to form allenylidene tetrahydroquinolines. The cyclocondensations are catalyzed by a variety of Brønsted acids, among which phosphoric acids provide the highest yields. Subsequent intramolecular and intermolecular additions to the allene moiety provide complex polycyclic amines.

  氨基炔丙基硅烷与羰基化合物缩合形成亚胺，然后环化形成亚烯基四氢喹啉。各种布朗斯台德酸催化环缩合反应，其中磷酸的收率最高。随后向丙二烯部分的分子内和分子间加成提供了复杂的多环胺。
• Stereoselective Synthesis of 3-Alkylideneoxindoles using Tandem Indium-Mediated Carbometallation and Palladium-Catalyzed Cross-Coupling Reactions
  作者：Reiko Yanada、Shingo Obika、Yusuke Kobayashi、Tsubasa Inokuma、Munetaka Oyama、Kazuo Yanada、Yoshiji Takemoto

  DOI：10.1002/adsc.200505147

  日期：2005.10

  the stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium-mediated carbometallation and palladium-catalyzed cross-coupling reactions. The proper combination of substrates and reaction conditions is important for good yields. The key step is the first stereoselective carboindation reaction using

  使用串联铟介导的碳金属化和钯催化的交叉偶联反应，研究了通过自由基环化反应立体选择性合成各种（E）-，（Z）-和二取代的3-亚烷基氧亚吲哚的第一种有效方法。底物和反应条件的适当组合对于获得良好的收率很重要。关键步骤是利用铟阳离子与酰胺羰基氧的强配位能力进行的第一个立体选择性碳氢化反应。我们将此方法应用于TMC-95A前体的合成。N-羟基邻苯二甲酰亚胺-O 2 -Co（OAc）2 -Mn（OAc）的N-脱苄基反应新方法还使用单电子氧化程序开发了图2。
• Synthesis of Functionalized Spiroaziridine-oxindoles from 3-Ylideneoxindoles: An Easy Route to 3-(Aminoalkyl)oxindoles
  作者：I. Ammetto、T. Gasperi、M. Antonietta Loreto、A. Migliorini、F. Palmarelli、P. Antonio Tardella

  DOI：10.1002/ejoc.200900891

  日期：2009.12

  Novel potentially bioactive spiroaziridine-oxindoles have been prepared by treatment of easily accessible 3-ylideneoxindoles with N-[(4-nitrophenyl)sulfonyl]oxy}carbamate (NsONHCO2Et) in the presence of CaO. These compounds gave new 3-(aminoalkyl)oxindole derivatives through easy and regioselective reductive aziridine ring-opening reactions.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  通过在 CaO 存在下用 N-[(4-硝基苯基)磺酰基]氧基}氨基甲酸酯 (NsONHCO2Et) 处理容易获得的 3-ylideneoxindoles，制备了新型的具有潜在生物活性的螺氮丙啶-oxindoles。这些化合物通过简单且区域选择性的还原性氮丙啶开环反应生成了新的 3-（氨基烷基）羟吲哚衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）
• Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and -δ-lactams
  作者：M. Antonietta Loreto、Antonella Migliorini、P. Antonio Tardella、Augusto Gambacorta

  DOI：10.1002/ejoc.200601034

  日期：2007.5

  New potentially bioactive α-spiroaziridino-γ- and -δ-lactams have been prepared by treatment of α-methylene-γ- and -δ-lactams with ethyl N-[(4-nitrophenyl)sulfonyl]oxy}carbamate (NsONHCO2Et) in the presence of CaO. These compounds, through reductive aziridine ring opening, can be intermediates for the synthesis of α- and β-aminolactams, which are useful as conformational constraints in peptides. The

  通过用 N-[(4-硝基苯基)磺酰基]氧基}氨基甲酸乙酯 (NsONHCO2Et) 处理 α-亚甲基-γ- 和 -δ-内酰胺制备了新的具有潜在生物活性的 α-螺环氮丙啶-γ- 和 -δ-内酰胺在 CaO 存在下。这些化合物通过还原氮丙啶开环，可以成为合成 α- 和 β-氨基内酰胺的中间体，可用作肽中的构象约束。上述过程已成功扩展到一种α-亚甲基吲哚，从而获得一种新的螺羟吲哚衍生物，一种潜在的天然生物碱前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Pin1-Modulating compounds and methods of use thereof
  申请人：Suto K. Robert

  公开号：US20060106077A1

  公开（公告）日：2006-05-18

  The invention is directed to modulators, e.g., inhibitors, of Pin1 and Pin1-related proteins and the use of such modulators for treatment of Pin1 associated states, e.g., for the treatment of cancer.

  本发明涉及Pin1和Pin1相关蛋白的调节剂，如抑制剂，以及使用这种调节剂治疗Pin1相关状态，如治疗癌症。