1-乙酰基-3,3-二甲基二氢吲哚-2-酮 | 72934-84-0

• 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: 1-乙酰基-3,3-二甲基二氢吲哚-2-酮
• 英文名称: 1-acetyl-3,3-dimethylindolin-2-one
• 英文别名: 1-Acetyl-3,3-dimethyl-indolin-2-on；1-acetyl-3,3-dimethyl-1,3-dihydroindol-2-one；1-acetyl-3,3-dimethylindol-2-one
• CAS: 72934-84-0
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: WSBBBRWBBKHEFG-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  383.6±31.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙酰基-3,3-二甲基二氢吲哚-2-酮 在 盐酸 、 三氯化铝 、 乙酸酐 、 N,N-二甲基甲酰胺 作用下， 反应 2.5h， 生成 5-(3-Dimethylamino-2-methyl-propionyl)-3,3-dimethyl-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Dihydropyridazinone cardiotonics. The discovery and inotropic activity of 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one

  摘要：

  We discovered that 6 (N-[4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl]acetamide) is a potent positive inotrope in dogs, and we have prepared several lactam analogues of this agent. These included 16 (1,3-dihydro-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one), 32 (the analogous quinolin-2-one), and 37 (the analogous benzazepin-2-one). The inotropic ED50's of these compounds were 24, 3.3, and 5.2 micrograms/kg, respectively, after iv administration to pentobarbital-anesthetized dogs. Compound 20 (LY195115, 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-i ndol-2- one), the geminal dimethyl analogue of 16, was 3.5-fold more potent than 16 when administered iv (ED50 = 6.8 micrograms/kg). However, the most profound effect of the geminal alkyl substitution was on oral activity. The approximate ED50's of 20 and 16 after oral administration to conscious dogs were 25 and 400 micrograms/kg, respectively. The increase in contractility produced by 25 micrograms/kg of 20 was maximally sustained in excess of 8 h. Thus, 20 is one of the most potent and long-acting oral inotropes described to date.

  DOI：

  10.1021/jm00160a006
• 作为产物：
  描述：

  1-(2,3-二甲基吲哚-1-基)乙酮 在 bis(trideuterodimethyl)dioxirane 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 1-乙酰基-3,3-二甲基二氢吲哚-2-酮
  参考文献：
  名称：

  单线态氧和二甲基二环氧乙烷氧化吲哚：通过氮酰化作用稳定化，以分离吲哚二氧环乙烷和环氧化物

  摘要：

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。

  DOI：

  10.1016/s0040-4039(00)73964-5

文献信息

• N-linked heterocyclic antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
  申请人：Qiao Jennifer

  公开号：US20060293281A1

  公开（公告）日：2006-12-28

  The present invention provides novel ureas containing N-aryl or N-heteroaryl substituted heterocycles of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, B, D and W are as defined herein. These compounds are selective inhibitors of the human P2Y 1 receptor which can be used as medicaments.

  本发明提供了含有式(I)的N-芳基或N-杂芳基取代的杂环的新型脲类化合物： 或其立体异构体、互变异构体、药学上可接受的盐或溶剂化合物形式，其中变量A、B、D和W如本文所定义。这些化合物是人类P2Y1受体的选择性抑制剂，可用作药物。
• Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
  申请人：Tuerdi Huji

  公开号：US20050261244A1

  公开（公告）日：2005-11-24

  The present invention provides novel ureas containing N-aryl or N-heteroaryl substituted heterocycles and analogues thereof, which are selective inhibitors of the human P2Y 1 receptor. The invention also provides for various pharmaceutical compositions of the same and methods for treating diseases responsive to modulation of P2Y 1 receptor activity.

  本发明提供了含有N-芳基或N-杂环芳基取代的杂环化合物及其类似物的新型脲类化合物，这些化合物是人类P2Y1受体的选择性抑制剂。该发明还提供了相应的各种药物组合物以及调节P2Y1受体活性治疗对其敏感的疾病的方法。
• Synthesis of Indole Derivatives by [2 + 2] Photocycloaddition of Indoline-2-thiones with alkenes and photodesulfurization of indoline-2-thiones
  作者：Takehiko Nishio、Mitsuru Oka

  DOI：10.1002/hlca.19970800205

  日期：1997.3.24

  The photochemical synthesis of indole derivatives starting from the indoline-2-thiones 1 is described. Irradiation of indoline-2-thiones 1 in the presence of alkenes 3 gave 2-alkyl-3H-indoles 4–7 or 2-alkylindoles 8–22 through the ring cleavage of the intermediates, spirocyclic amino-thietanes, initially derived by [2 + 2] cycloaddition of the CS bond of 1 and the CC bond of 3. Irradiation of 1 in

  描述了从二氢吲哚-2-硫酮1开始的吲哚衍生物的光化学合成。二氢吲哚-2-硫酮的照射1在烯烃的存在下3，得到2-烷基-3- ħ -indoles 4 - 7或2-烷基吲哚8 - 22穿过中间体的环切割，螺环氨基thietanes，最初由衍生[ [2 + 2]的1个CS键和3的CC键的环加成。在三烷基胺26存在下辐照1可获得脱硫产物27 – 32和意外的3-烷基吲哚33 – 40。Ñ -Acylindoline -2-硫酮11 - p，得到去酰基化的产品，二氢吲哚-2-硫酮1A - b，和乙酯43在CDC1照射时通过γ-H提取由激发硫代酰胺S-原子3 / EtOH或苯/乙醇 氧类似物2a - d也经过分子内H提取，以类似方式得到吲哚2-2-酮2e - f和乙酯43。
• NOVEL COMPOUNDS
  申请人：Gottschling Dirk

  公开号：US20110195954A1

  公开（公告）日：2011-08-11

  The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R 1 , R 2 , R 3 and R 4 are defined as mentioned in the description, the tautomers thereof, the isomers thereof, the diastereomers thereof, the enantiomers thereof, the hydrates thereof, the mixtures thereof and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, the use thereof and processes for the preparation thereof.

  本发明涉及一般式I的新CGRP拮抗剂，其中U、V、X、Y、R1、R2、R3和R4如描述中所述定义，其互变异构体、异构体、顺反异构体、对映异构体、水合物、混合物及其盐，以及其盐的水合物，特别是与无机或有机酸或碱形成的生理上可接受的盐，包含这些化合物的药物、其用途以及其制备方法。
• Oxidation of indoles by singlet oxygen and dimethyldioxirane: Isolation of indole dioxetanes and epoxides by stabilization through nitrogen acylation
  作者：Waldemar Adam、Michael Ahrweiler、Markus Sauter、Bernd Schmiedeskamp

  DOI：10.1016/s0040-4039(00)73964-5

  日期：1993.8

  through N-acylation allowed the isolation of the labile indole dioxetanes 2, which were transformed by dimethyl sulfide deoxygenation to the corresponding indole epoxides 5; the latter were also independently prepared by dimethyldioxirane oxidation.

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。