3-(4-methoxyl-benzylidene)-1-methyl-1,3-dihydro-indol-2-one | 34219-45-9

• 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: 3-(4-methoxyl-benzylidene)-1-methyl-1,3-dihydro-indol-2-one
• 英文别名: (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate；(E)-3-(4-methoxybenzylidene)-1-methylindolin-2-one；(3E)-3-[(4-methoxyphenyl)methylidene]-1-methylindol-2-one
• CAS: 34219-45-9
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: TUDFJZORIQRAIY-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyl-benzylidene)-1-methyl-1,3-dihydro-indol-2-one 、 肌氨酸 、 靛红 在 zinc dibromide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(3R*,3″S*,4′R*)-4′-(4-methoxyphenyl)-1′,1″-dimethyldispiro[indole-3,2′-pyrrolidine-3′,3″-indole]-2,2″(1H,1″H)-dione
  参考文献：
  名称：

  10.3998/ark.5550190.p010.046

  摘要：

  DOI：

  10.3998/ark.5550190.p010.046
• 作为产物：
  描述：

  [(methyl-phenyl-carbamoyl)-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-methyl]-phosphonic acid diethyl ester 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 生成 3-(4-methoxyl-benzylidene)-1-methyl-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  One-Pot Homolytic Aromatic Substitutions/HWE Olefinations under Microwave Conditions for the Formation of a Small Oxindole Library

  摘要：

  An efficient one-pot sequence comprising a homolytic aromatic substitution followed by an ionic Horner-Wadsworth-Emmons olefination for the preparation of a small library of alpha,beta-unsaturated oxindoles is presented. Microwave-induced heating is used to conduct these reactions. The homolytic aromatic substitution is mediated by the persistent radical effect.

  DOI：

  10.1021/ol048759t

文献信息

• Palladium/Copper-Catalyzed Oxidative CH Alkenylation/N-Dealkylative Carbonylation of Tertiary Anilines
  作者：Renyi Shi、Lijun Lu、Hua Zhang、Borui Chen、Yuchen Sha、Chao Liu、Aiwen Lei

  DOI：10.1002/anie.201303911

  日期：2013.9.27

  CH/CN activation: The first palladium/copper‐catalyzed aerobic oxidative CH alkenylation/N‐dealkylative carbonylation of tertiary anilines has been developed. Various functional groups were tolerated and acrylic ester could also be suitable substrates. This transformation provided efficient and straightforward synthesis of biologically active 3‐methyleneindolin‐2‐one derivatives from cheap and simple

  Ç  H / C  Ñ活化：第一钯/铜催化氧化好氧Ç  ħ烯基/ Ñ叔苯胺-dealkylative羰基化得到了发展。可以容忍各种官能团，丙烯酸酯也可以用作合适的底物。这种转化提供了从廉价，简单的底物中高效，直接地合成具有生物活性的3-亚甲基吲哚-2-酮衍生物的功能。
• Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756
  作者：Jana Lubkoll、Alessia Millemaggi、Alexis Perry、Richard J.K. Taylor

  DOI：10.1016/j.tet.2010.03.018

  日期：2010.8

  developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability

  已经开发了一个串联序列，涉及霍纳-沃兹沃思-埃蒙斯（HWE）烯化反应，然后进行钯催化的分子内Heck反应，以提供从α-卤代苯胺快速获得3-烯基-氧吲哚的途径。这种一锅微波加速方法是使用乙酸乙酸钯（II）或四（三苯基膦）钯催化的，已用于制备一系列衍生自芳族，杂芳族和脂族醛的加合物。该方法可用于直接制备N-未保护的羟吲哚，并且该方法的适用性通过一锅合成塞马克尼（一种血管生成信号抑制剂）和GW441756（一种氮杂-羟吲哚Trk A抑制剂）来建立。
• One-Pot Synthesis of Dispiro[oxindole-3,3′-pyrrolidines] by Three-Component [3+2] Cycloadditions of<i>in situ</i>-Generated Azomethine Ylides with 3-Benzylidene-2,3-dihydro-1<i>H</i>-indol-2-ones
  作者：Firouz Matloubi Moghaddam、Mostafa Kiamehr、Mohammad Reza Khodabakhshi、Marjan Jebeli Javan、Shaghayegh Fathi、Alexander Villinger、Viktor O. Iaroshenko、Peter Langer

  DOI：10.1002/hlca.201200602

  日期：2013.11

  An efficient one‐pot, three‐component synthesis of novel dispiro[oxindole‐3,3′‐pyrrolidines] by 1,3‐dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2‐diones with sarcosine and subsequent decarboxylation, with a series of (E)‐3‐benzylidene‐2,3‐dihydro‐1H‐indol‐2‐ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent

  1,2-二酮与肌氨酸的反应及随后的脱羧反应原位生成偶氮甲亚胺的1,3-偶极环加成反应，从而有效地一锅三组分合成新型双螺[oxindole-3,3'-吡咯烷] ，报告了一系列（E）-3-亚苄基-2,3-二氢-1 H-吲哚-2-酮。分子复杂性仅在一个合成步骤中产生。所有反应均以优异的区域选择性和良好至优异的产率进行。后处理容易，反应时间短，并且不需要催化剂。
• Palladium-catalyzed oxidative arylation of trisubstituted olefin: an efficient synthesis of 3-(disubstituted)alkylidene-oxindoles
  作者：Hyun Ju Lee、Ko Hoon Kim、Se Hee Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2012.10.122

  日期：2013.1

  A palladium-catalyzed oxidative arylation of 3-(monosubstituted)alkylidene-oxindoles with arenes afforded 3-(disubstituted)alkylidene-oxindoles in good to moderate yields. (C) 2012 Elsevier Ltd. All rights reserved.
• One-Pot Homolytic Aromatic Substitutions/HWE Olefinations under Microwave Conditions for the Formation of a Small Oxindole Library
  作者：Antje Teichert、Katja Jantos、Klaus Harms、Armido Studer

  DOI：10.1021/ol048759t

  日期：2004.9.1

  An efficient one-pot sequence comprising a homolytic aromatic substitution followed by an ionic Horner-Wadsworth-Emmons olefination for the preparation of a small library of alpha,beta-unsaturated oxindoles is presented. Microwave-induced heating is used to conduct these reactions. The homolytic aromatic substitution is mediated by the persistent radical effect.