(E)-1-methyl-3-(2-oxopropylidene)indolin-2-one | 70351-51-8

• 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)-1-methyl-3-(2-oxopropylidene)indolin-2-one
• 英文别名: 3-((E)-acetonylidene)-1-methyl-indolin-2-one；3-((E)-Acetonyliden)-1-methyl-indolin-2-on；(3E)-1-methyl-3-(2-oxopropyridene)-1,3-dihydro-2H-indol-2-one；Supercinnamaldehyde；(3E)-1-methyl-3-(2-oxopropylidene)indol-2-one
• CAS: 70351-51-8
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: CZKBLHCEDVWPRN-JXMROGBWSA-N

物化性质

• 溶解度：
  DMSO：可溶10mg/mL，澄清

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37,S61
• 危险类别码：
  R36/37/38,R52/53

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-3-(2-oxopropylidene)indolin-2-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以18%的产率得到(3Z)-1-甲基-3-(2-氧代亚丙基)-1,3-二氢-2H-吲哚-2-酮
  参考文献：
  名称：

  一种容易的路易斯酸介导的从（E）-到（Z）-羟吲哚-3-亚基酮的异构化反应。

  摘要：

  在室温下，CH 2 Cl 2中的AlCl 3可以很容易地将（E）-2-氧代吲哚-3-亚基酮异构化为（Z）异构体。（Z）-构型中作为二齿配体的不饱和二羰基骨架的行为可能是异构化的关键步骤。讨论了可以制备几种尚不知道的产物的反应极限。

  DOI：

  10.1016/s0040-4020(01)85706-9
• 作为产物：
  描述：

  3-羟基-1-甲基-3-(2-氧代丙基)-1,3-二氢-2H-吲哚-2-酮 在 盐酸 、 乙醇 、 水 作用下， 生成 (E)-1-methyl-3-(2-oxopropylidene)indolin-2-one
  参考文献：
  名称：

  Condensations of Isatin with Acetone by the Knoevenagel Method¹

  摘要：

  DOI：

  10.1021/ja01328a041

文献信息

• INDOLINONE COMPOUND
  申请人：Kaku Hidetaka

  公开号：US20110009379A1

  公开（公告）日：2011-01-13

  [Problems] A compound, which is useful as an active ingredient for a pharmaceutical composition, for example a pharmaceutical composition for treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder, is provided. [Means for Solution] The present inventors have extensively studied compounds having TRPA1 channel activation activity, and confirmed that an indolinone compound has a TRPA1 channel activation activity, and thus completed the present invention. The indolinone compound of the present invention has a TRPA1 channel activation activity and can be used as an active ingredient of a pharmaceutical composition for preventing and/or treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder or the like.

  [问题] 提供一种化合物，该化合物可用作制药组合物的活性成分，例如用于治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍的制药组合物。 [解决方案] 现有发明人广泛研究了具有TRPA1通道激活活性的化合物，并确认一种吲哚酮化合物具有TRPA1通道激活活性，从而完成了本发明。本发明的吲哚酮化合物具有TRPA1通道激活活性，可用作预防和/或治疗便秘型肠易激综合征，弛缓性便秘和/或功能性胃肠障碍等制药组合物的活性成分。
• Acid‐Controlled Regional Diverse Synthesis of CF₃‐Containing Ketoimines and Application in the Construction of Bispiro[oxindole‐pyrrolidine‐benzothiophenone]s
  作者：Shuo Sun、Danna Chen、Hai Guo、Yinghui Liu、Xia Liu、Wenjin Yan、Jinqi Huang

  DOI：10.1002/ejoc.202300586

  日期：2023.8.14

  Here described an acid‐controlled regional diverse synthesized process of CF₃‐containing ketoimines by the condensation of benzo[b]thiophene‐2,3‐dione and 2,2,2‐trifluoroethlamine. The imines obtained at either the 2‐position or 3‐position can be further used as substrates in asymmetric organocatalyzed [3+2]‐cycloaddition reactions, leading to a library of regiodiverse bispiro‐compounds with 85–96 % yield and 65–99 % ee.

  摘要本文介绍了通过苯并[b]噻吩-2,3-二酮和 2,2,2-三氟乙胺缩合合成含 CF3 酮亚胺的酸控区域多样性过程。在 2 位或 3 位上得到的亚胺可进一步用作不对称有机催化 [3+2] - 环加成反应的底物，从而得到一个具有 85-96 % 收率和 65-99 % ee 的多区域双环化合物库。
• Design and synthesis of marine natural product-based 1H-indole-2,3-dione scaffold as a new antifouling/antibacterial agent against fouling bacteria
  作者：Mahesh S. Majik、Cheryl Rodrigues、Stacey Mascarenhas、Lisette D’Souza

  DOI：10.1016/j.bioorg.2014.05.001

  日期：2014.6

  Marine organisms such as seaweeds, sponges and corals protect their own surfaces from fouling by their high anesthetic, repellant, and settlement inhibition properties. Within the marine ecosystem, evolution has allowed for the development of certain antifouling properties. Isatin is a biologically active chemical produced by an Alteromonas sp. strain inhibiting the surface of embryos of the cardiean shrimp Palaemon macrodectylus, which protect them from the pathogenic fungus Lagenidium callinectes. In present study, an antibacterial activity of isatin and its synthetic analogues were evaluated against different fouling bacteria in order to explore the structure activity relationships for the first time. The synthesized compounds along with parent isatin were tested against different ecologically relevant marine microorganisms by using the Kirby-Bauer disc diffusion method. Few synthetically modified isatin exhibited potent inhibitory activity at concentration of 2 mu g/disc against Planococcus donghaensis, Erythrobacter litoralis, Alivibrio salmonicida, Vibrio furnisii. Overall, the modified analogues showed stronger activity than the parent marine natural product (isatin) and hence 1H-indole-2,3-dione scaffold has immense potential as future antibacterial/antifouling candidate. (C) 2014 Elsevier Inc. All rights reserved.
• Giuseppe Faita, Mariella Mella, PierPaolo Righetti*, Gianfranco Tacconi, Tetrahedron, 50 (1994) N 37, S 10955-10962
  作者：Giuseppe Faita, Mariella Mella, PierPaolo Righetti*, Gianfranco Tacconi

  DOI：——

  日期：——
• USE OF TRP CHANNEL AGONISTS TO TREAT INFECTIONS
  申请人：Hava David L.

  公开号：US20130203715A1

  公开（公告）日：2013-08-08

  Methods are described for treating or preventing a respiratory infection by administering an effective amount of a TRP channel agonist.