(2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 | 2971-31-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸
• 英文名称: 2,3-dihydro-2-oxo-1H-indole-3-acetic acid
• 英文别名: (2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid；2-(2-oxo-1,3-dihydroindol-3-yl)acetic acid；2-(2-oxoindolin-3-yl)acetic acid；2-(2-oxo-3-indolyl)acetic acid；2-(oxindol-3-yl)acetic acid；2-oxindol-3-yl-acetic acid
• CAS: 2971-31-5
• 化学式: C₁₀H₉NO₃
• mdl: MFCD09035909
• 分子量: 191.186
• InChiKey: ILGMGHZPXRDCCS-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  445.2±38.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20℃，干燥，密封

反应信息

• 作为反应物：
  描述：

  (2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-O-(2-oxoindol-3-ylacetyl)-β-D-glucopyranose
  参考文献：
  名称：

  Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana

  摘要：

  Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-beta-D-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-elect ro spray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these;imino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.04.030
• 作为产物：
  描述：

  3-吲哚乙酸 在 盐酸 、 二甲基亚砜 作用下， 以 水 为溶剂， 反应 0.5h， 以51%的产率得到(2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸
  参考文献：
  名称：

  氧化吲哚衍生物的氧化碎片和骨架重排

  摘要：

  通过铜催化的CHH过氧化和随后的碱介导的裂解反应的组合，揭示了将羟吲哚转化为结构上不同的杂环骨架和苯胺衍生物的氧化顺序。与经典的酶促方法（即犬尿氨酸途径）和仿生方法（即Witkop–Winterfeldt氧化法）进行氧化吲哚裂解不同，该方案允许引入外部亲核试剂。新的转化显示出广泛的官能团耐受性，适用于色氨酸衍生物，为多肽的后合成修饰，生物缀合和非天然氨基酸合成开辟了潜在的新途径。

  DOI：

  10.1021/acs.orglett.6b03789

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT OF HIV<br/>[FR] COMPOSÉS POUR TRAITER LE VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2013006738A1

  公开（公告）日：2013-01-10

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

  本发明提供了如下式（I）的化合物或其盐，还提供了包含如下式（I）化合物的药物组合物，制备如下式（I）化合物的方法，用于制备如下式（I）化合物的中间体以及治疗Retroviridae病毒感染的治疗方法，包括由HIV病毒引起的感染。
• Glycine receptor antagonist pharmacophore
  申请人：State of Oregon, Acting by and through the Oregon State Board of Higher

  公开号：US05597922A1

  公开（公告）日：1997-01-28

  Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.

  通过向需要此类治疗的动物投药，揭示了治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失的方法，以及治疗包括阿尔茨海默病、肌萎缩侧索硬化症、亨廷顿病和唐氏综合症在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度活跃的不良后果，以及治疗焦虑、慢性疼痛、惊厥和诱导麻醉的方法是通过给予具有高结合到甘氨酸受体的化合物。
• Iron-Catalyzed Batch/Continuous Flow C–H Functionalization Module for the Synthesis of Anticancer Peroxides
  作者：Moreshwar B. Chaudhari、Suresh Moorthy、Sohan Patil、Girish Singh Bisht、Haneef Mohamed、Sudipta Basu、Boopathy Gnanaprakasam

  DOI：10.1021/acs.joc.7b02854

  日期：2018.2.2

  with aliphatic peroxide was developed under mild conditions. A library of linear alkylated and arylated peroxides are synthesized in good to excellent yield. This method is highly selective and general for a range of biologically important derivatives of 2-oxindole, barbituric acid, and 4-hydroxy coumarin with a good functional group tolerance and without the cleavage of the peroxide bond. This peroxidation

  在温和条件下开发了铁催化的羰基化合物与脂肪族过氧化物的脱氢交叉偶联反应。合成直链烷基化和芳基化的过氧化物的库具有良好至极好的收率。该方法对2-氧吲哚，巴比妥酸和4-羟基香豆素具有重要的官能团耐受性且没有过氧化物键的裂解的生物学上重要的一系列衍生物具有高度的选择性和通用性。该过氧化反应可升级至克级，并且还可以在连续流中合成，并且在短时间内提高了安全性。机理研究表明，Fe-（II）经历了氧化还原型过程以生成自由基中间体，该中间体随后选择性地重组以形成稳定的过氧化物。50 = 5.3μM。
• Regioselective oxidation of indoles to 2-oxindoles
  作者：Santosh V. Shelar、Narshinha P. Argade

  DOI：10.1039/c9ob00764d

  日期：——

  Facile regioselective oxidation of indoles to 2-oxindoles promoted by sulfuric acid adsorbed on silica gel is reported. The demonstrated practical site-selective heterogeneous oxidation reactions conveniently take place with a broad substrate scope and functional group tolerances. The present oxidation strategy is also employed to accomplish the total synthesis of natural products donaxaridine and

  据报道，通过硫酸吸附在硅胶上，吲哚易于区域选择性氧化为2-羟吲哚。在广泛的底物范围和官能团耐受性的情况下，已证明的实用的现场选择性非均相氧化反应可以方便地进行。本发明的氧化策略也被用来完成天然产物多那西啶和多那沙林的全合成。根据分析和光谱数据，证明多纳沙林与其水合开环形式保持平衡。简要讨论了这种类型的氧化必不可少的结构特征和合理的机理。
• [EN] CONJUGATES OF AUXIN ANALOGS<br/>[FR] CONJUGUÉS D'ANALOGUES D'AUXINE
  申请人：THE STATE OF ISRAEL MINISTRY OF AGRICULTURE & RURAL DEVELOPMENT AGRICULTURAL RES ORGANIZATION ARO VO

  公开号：WO2020212993A1

  公开（公告）日：2020-10-22

  Described herein are methods of enhancing formation and/or growth of an adventitious root in a plant and/or plant tissue, and/or for promoting grafting unification, enhancing fruit size and/or reducing flowering in a plant. The method comprises contacting at least a portion of the plant and/or plant tissue with a compound having Formula (I): wherein X, Y and R1-R7 are as defined herein. Further described are compositions for enhancing formation and/or growth of an adventitious root in a plant and/or plant tissue, and/or for promoting grafting unification, enhancing fruit size and/or reducing flowering in a plant, comprising the abovementioned compound and a horticulturally acceptable carrier. Novel compounds having Formula I are also described herein.

  本文描述了增强植物和/或植物组织中顺式根的形成和/或生长，促进嫁接联合，增强果实大小和/或减少植物开花的方法。该方法包括将至少植物和/或植物组织的一部分与具有公式（I）的化合物接触：其中X、Y和R1-R7如本文所定义。还描述了用于增强植物和/或植物组织中顺式根的形成和/或生长，促进嫁接联合，增强果实大小和/或减少植物开花的组合物，包括上述化合物和园艺上可接受的载体。本文还描述了具有公式I的新化合物。