2-(1-甲基-1H-吲哚-3-基)-2-氧代乙酰胺 | 16382-39-1

• 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-(1-甲基-1H-吲哚-3-基)-2-氧代乙酰胺
• 英文名称: 2-(1-methyl-1H-indol-3-yl)-2-oxoacetamide
• 英文别名: 1-methylindolyl-3-α-oxoacetamide；N-methylindole-3-glyoxylamide；(1-methyl-indol-3-yl)-glyoxylic acid amide；(1-Methyl-indol-3-yl)-glyoxylsaeure-amid；1-Methylindol-3-glyoxylamid；2-(1-methylindol-3-yl)-2-oxoacetamide
• CAS: 16382-39-1
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: NHABXENRVFNROZ-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: isopropanol (67-63-0))
• 沸点：
  422.1±37.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  65.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  2-(1-甲基-1H-吲哚-3-基)-2-氧代乙酰胺 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以97%的产率得到1-methylindolyl-3-carbonylnitrile
  参考文献：
  名称：

  A new synthesis of versatile indolyl-3-carbonylnitriles

  摘要：

  Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources Of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible alpha-oxoacetamides in generally high yields under simple reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.075
• 作为产物：
  描述：

  1-methylindole-3-glyoxylyl chloride 在 ammonium hydroxide 作用下， 反应 0.5h， 以3.83 g的产率得到2-(1-甲基-1H-吲哚-3-基)-2-氧代乙酰胺
  参考文献：
  名称：

  A Practical Method for the Synthesis of Indolylaryl- and Bisindolylmaleimides

  摘要：

  Indolylaryl and indolylheteroarylmaleimides, including bisindolylmaleimides, are easily prepared by the reaction of N-methylindole-3-glyoxylamide with methyl aryl acetates in the presence of potassium tert-butoxide in THF.

  DOI：

  10.1021/ol0621203

文献信息

• Copper(II)-Mediated Aerobic Oxidation of Benzylimidates: Synthesis of Primary α-Ketoamides
  作者：Yogesh Kumar、Mukta Shaw、Rima Thakur、Amit Kumar

  DOI：10.1021/acs.joc.6b01262

  日期：2016.8.5

  A simple and straightforward method for the synthesis of primary α-ketoamides has been discovered. The reaction represents the first example of benzylimidates directly converting to primary α-ketoamides by using sustainable molecular oxygen as an oxidant. This reaction proceeds in the presence of copper(II) salt via cleavage of benzylic C–H and C–O bonds of the benzylimidates with liberation of alcohols

  已经发现一种简单直接的合成伯α-酮酰胺的方法。该反应代表了通过使用可持续的分子氧作为氧化剂将亚氨基苄基酯直接转化为伯α-酮酰胺的第一个例子。该反应在铜盐（II）的存在下通过裂解亚氨酸苄基的苄基C–H和C–O键进行，唯一的副产物是醇的释放。广泛的底物范围，操作温和的条件，使用单个底物以及放大至克数的反应，使得该策略非常具有吸引力和实用性。此外，机理研究表明，与苄基位置相邻的亚氨酸酯基团在促进该化学过程中起着至关重要的作用。
• Formamidine hydrochloride as an amino surrogate: I₂-catalyzed oxidative amidation of aryl methyl ketones leading to free (N–H) α-ketoamides
  作者：Shan Liu、Qinghe Gao、Xia Wu、Jingjing Zhang、Kerong Ding、Anxin Wu

  DOI：10.1039/c4ob02591a

  日期：——

  A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones has been developed. This reaction represents a novel strategy for the synthesis of free (N–H) α-ketoamides.

  已开发出一种高效的分子碘催化的芳基甲基酮氧化酰胺化反应。该反应代表了合成自由(N-H) α-酮酰胺的新颖策略。
• Reduction of carbonylic radicals in indolyl-3 compounds
  申请人：UPJOHN CO

  公开号：US02825734A1

  公开（公告）日：1958-03-04
• The first synthesis of [11C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3)
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2010.11.026

  日期：2011.1

  SB-216763 is a novel, potent and selective glycogen synthase kinase-3 (GSK-3) inhibitor with an IC50 value of 34 nM. [C-11]SB-216763 (3-(2,4-dichlorophenyl)-4-(1-[C-11]methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione), a new potential PET agent for imaging of GSK-3, was first designed and synthesized in 20-30% decay corrected radiochemical yield and 370-555 GBq/mu mol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled maleic anhydride intermediate followed by the conversion to maleimide. (C) 2010 Elsevier Ltd. All rights reserved.
• Use of FAAH Inhibitors for Treating Parkinson's Disease and Restless Legs Syndrome
  申请人：Pearson James Philip

  公开号：US20130150346A1

  公开（公告）日：2013-06-13

  The present disclosure relates to methods of using fatty acid amide hydrolase (FAAH) inhibitors to treat aspects of Parkinson's disease (PD), restless legs syndrome (RLS) and periodic limb movement disorder (PLMD), the use of FAAH inhibitors for the manufacture of medicaments for use in the treatment of PD, RLS and PLMD, as well as pharmaceutically acceptable compositions comprising FAAH inhibitors for use in the treatment of PD, RLS and PLMD.