3-hydroxy-3-(2-oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one | 70452-28-7

• 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-hydroxy-3-(2-oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one
• 英文别名: 3-Hydroxy-3-(3'-pyridyl)acyloxindol；3-hydroxy-3-(2-oxo-2-pyridin-3-ylethyl)-1H-indol-2-one
• CAS: 70452-28-7
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: AHXRLADLJSXWQH-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  564.2±50.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(2-oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one 在 氯化亚砜 、 sodium dithionite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.17h， 生成 3-(2-Oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis of [a]annulated carbazoles from indol-2,3-dione

  摘要：

  Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3-[(2-aryl-2-ethoxycarbonyloxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding [a]annulated carbazoles 10 are obtained via 6pi-electrocyclization.

  DOI：

  10.1016/s0040-4020(01)81301-6
• 作为产物：
  描述：

  3-乙酰基吡啶 、 靛红 在 二乙胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 3-hydroxy-3-(2-oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

  摘要：

  通过NMR光谱对3-酰基吲哚类化合物中E/Z几何异构体的命名可能会导致不正确的烯烃立体化学分配，因为在一系列大类类似物中观察到的化学位移范围较窄。相较之下，UV-Vis光谱为烯烃立体化学分配提供了一种方便且更可靠的方法。X射线晶体学与理论研究的结合表明，UV-Vis光谱行为的观察差异与Z-异构体的扭曲构象有关，该构象相对于E-异构体提供了降低的共轭效应和较弱的紫外光移吸收。

  DOI：

  10.1039/c4ob00496e

文献信息

• Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions
  作者：Makafui Gasonoo、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2015.06.028

  日期：2015.8

  The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or anisole, the Friedel–Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving carbocationic electrophiles leading to the aromatic substitution chemistry.

  已经制备了一系列丙酮基取代的3-羟基-2-氧吲哚，并与芳烃在超酸促进的Friedel-Crafts反应中反应。产物芳基取代的2-氧吲哚通常以良好的产率形成。对于取代的芳烃，例如甲苯，溴苯或苯甲醚，Friedel-Crafts反应的区域选择性极好。提出了涉及碳阳离子亲电试剂导致芳族取代化学的机理。
• Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2
  作者：Cornelius Klöck、Xi Jin、Kihang Choi、Chaitan Khosla、Peter B. Madrid、Andrew Spencer、Brian C. Raimundo、Paul Boardman、Guido Lanza、John H. Griffin

  DOI：10.1016/j.bmcl.2010.12.037

  日期：2011.5

  Inhibitors of human transglutaminase 2 (TG2) are anticipated to be useful in the therapy of a variety of diseases including celiac sprue as well as certain CNS disorders and cancers. A class of 3-acylidene-2-oxoindoles was identified as potent reversible inhibitors of human TG2. Structure-activity relationship analysis of a lead compound led to the generation of several potent, competitive inhibitors. Analogs with significant non-competitive character were also identified, suggesting that the compounds bind at one or more allosteric regulatory sites on this multidomain enzyme. The most active compounds had K(i) values below 1.0 mu M in two different kinetic assays for human TG2, and may therefore be suitable for investigations into the role of TG2 in physiology and disease in animals. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of [a]annulated carbazoles from indol-2,3-dione
  作者：Egle M. Beccalli、Alessandro Marchesini、Tullio Pilati

  DOI：10.1016/s0040-4020(01)81301-6

  日期：1993.5

  Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3-[(2-aryl-2-ethoxycarbonyloxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding [a]annulated carbazoles 10 are obtained via 6pi-electrocyclization.
• Studies on the stereochemical assignment of 3-acylidene 2-oxindoles
  作者：Steven J. Edeson、Julong Jiang、Stephen Swanson、Panayiotis A. Procopiou、Harry Adams、Anthony J. H. M. Meijer、Joseph P. A. Harrity

  DOI：10.1039/c4ob00496e

  日期：——

  The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

  通过NMR光谱对3-酰基吲哚类化合物中E/Z几何异构体的命名可能会导致不正确的烯烃立体化学分配，因为在一系列大类类似物中观察到的化学位移范围较窄。相较之下，UV-Vis光谱为烯烃立体化学分配提供了一种方便且更可靠的方法。X射线晶体学与理论研究的结合表明，UV-Vis光谱行为的观察差异与Z-异构体的扭曲构象有关，该构象相对于E-异构体提供了降低的共轭效应和较弱的紫外光移吸收。