(E)-3-(4-chlorobenzylidene)-1-methylindolin-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: (E)-3-(4-chlorobenzylidene)-1-methylindolin-2-one
• 英文别名: (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate；3-(4-chlorobenzylidene)-1-methylindolin-2-one；(3E)-3-[(4-chlorophenyl)methylidene]-1-methylindol-2-one
• 化学式: C₁₆H₁₂ClNO
• 分子量: 269.73
• InChiKey: IYRYQYLIWZUBKX-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-3-(4-chlorobenzylidene)-1-methylindolin-2-one 、 肌氨酸 、 靛红 在 zinc dibromide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到(3R*,3″S*,4′R*)-4′-(4-chlorophenyl)-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：

  2-indolinone 在 哌啶 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E)-3-(4-chlorobenzylidene)-1-methylindolin-2-one
  参考文献：
  名称：

  One-Step Synthesis of Highly Functionalized Monofluorinated Cyclopropanes from Electron-Deficient Alkenes

  摘要：

  The unique combination of Zn/LiCl allowed generation of reactive zinc enolate from ethyl dibromofluoroacetate. This fluorinated enolate reacts efficiently with a wide range of functionalized electron-deficient alkenes to afford the corresponding monofluorinated cyclopropylcarboxylates in good yields.

  DOI：

  10.1021/ol300687s

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。
• Combined Scaffold Evaluation and Systems‐Level Transcriptome‐Based Analysis for Accelerated Lead Optimization Reveals Ribosomal Targeting Spirooxindole Cyclopropanes
  作者：Kevin X. Rodriguez、Erin N. Howe、Emily P. Bacher、Miranda Burnette、Jennifer L. Meloche、Jayda Meisel、Patricia Schnepp、Xuejuan Tan、Mayland Chang、Jeremiah Zartman、Siyuan Zhang、Brandon L. Ashfeld

  DOI：10.1002/cmdc.201900266

  日期：2019.9.18

  paramount. In this study, we combined scaffold-directed synthesis with a hybrid experimental and transcriptome analysis to identify bis-spirooxindole cyclopropanes that inhibit cancer cell proliferation through disruption of ribosomal function. These findings demonstrate the value of an integrated, biologically inspired synthesis and assay strategy for the accelerated identification of first-in-class

  随着进化的耐药性影响治疗疾病的努力，对表现出新的分子作用机制的小分子的需求至关重要。在这项研究中，我们将支架导向的合成与混合实验和转录组分析相结合，以鉴定可通过破坏核糖体功能抑制癌细胞增殖的双螺氧并吲哚环丙烷。这些发现证明了一种综合的，生物学启发的合成和分析策略对于加速识别一流癌症治疗候选物的价值。
• Stereochemical implications in the synthesis of 3,3′-spirocyclopropyl oxindoles from β-aryl/alkyl-substituted alkylidene oxindoles
  作者：Erin E. Wilson、Kevin X. Rodriguez、Brandon L. Ashfeld

  DOI：10.1016/j.tet.2015.06.004

  日期：2015.9

  3,3'-Spirocyclopropane oxindoles were synthesized in good to excellent yield and diastereoselectivity employing a Kukhtin Ramirez reaction between readily accessible E-alkylidene oxindoles, commercially available P(NMe2)(3), and alpha-keto esters. The stereoselectivity in the cyclopropanation event can be traced to the starting alkylidene geometry and the propensity of the exocyclic alkene to undergo isomerization in the presence of an electron rich phosphine. (C) 2015 Elsevier Ltd. All rights reserved.