2-acetyl-3-hydroxyinden-1-one | 70450-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-acetyl-3-hydroxyinden-1-one
• 英文别名: 2-acetyl-1,3-indanedione；2-acetyl-1,2-indandione；2-acetyl-1,3-indandione；2-acetylindan-1,3-dione；2-AID
• CAS: 70450-80-5
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: SAOAMRWELDSISG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-hydroxyinden-1-one 在 triethylamine 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 Ag(2-acetyl-1,3-indandione(1-))*2(triphenylphosphine)
  参考文献：
  名称：

  含2-乙酰基-1,3-茚满二酮配体的有机膦/亚磷酸酯稳定的银（I）配合物的合成与表征，[Ph3P·AgC11H7O3]的晶体结构

  摘要：

  摘要六种Ln·AgC11H7O3型2-乙酰基1,3-茚满二酮（2-AID）的有机膦/亚磷酸酯稳定的银（I）配合物（L = PPh3; n = 1，2a; n = 2，2b; L = P [OMe）3; n = 1，2c; n = 2，2d; L = P（OEt）3; n = 1，2e; n = 2，2f）是通过[AgC11H7O3]反应制备的。通过使2-AID与AgNO3，三苯基膦，三甲基亚磷酸酯或亚磷酸三乙酯以1-2-2 M的比例反应获得。这些配合物以高收率获得，并分别通过元素分析，1H，13C {H} NMR，IR光谱和热分析（TG和DSC）进行表征。2a的分子结构已通过X射线单晶分析确定，其中银原子呈扭曲的三角几何形状。

  DOI：

  10.1016/j.poly.2010.02.017
• 作为产物：
  描述：

  1,3-茚满二酮 、 乙酸酐 在 4-二甲氨基吡啶 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以63%的产率得到2-acetyl-3-hydroxyinden-1-one
  参考文献：
  名称：

  Protecting and linking groups for organic synthesis on solid supports

  摘要：

  这项发明涉及有机化合物合成的方法，特别是用于合成肽、寡糖、糖肽和糖脂的保护和连接基团。该发明提供了在固相和溶液合成中均有用的保护和连接基团，特别适用于组合合成。

  公开号：

  US06765089B1

文献信息

• Novel green-yellow-orange-red light emitting donor-π-acceptor type dyes based on 1,3-indandione and dimedone moieties
  作者：Ilze Malina、Valdis Kampars、Baiba Turovska、Sergey Belyakov

  DOI：10.1016/j.dyepig.2017.01.017

  日期：2017.4

  Ten novel luminescent dyes containing 1,3-indandione or dimedone as electron acceptors, amino derivatives (dimethylamino, diphenylamino, julolidine and dibiphenylamino) as electron donor units and different length olefinic linkers (1-hydroxyallylidene or 1-hydroxypenta-2,4-dien-1-ylidene) are reported in this study. Newly synthesized compound structures are proven with X-ray analysis, 1H, 13C NMR spectroscopy

  十种新颖的发光染料，包含1,3-茚满二酮或二甲酮作为电子受体，氨基衍生物（二甲基氨基，二苯氨基，甲氧吡啶和二联苯氨基）作为电子供体单元和不同长度的烯烃接头（1-羟基亚烷基或1-羟基戊-2,4-二烯）在该研究中报道了-1-亚萘基）。X射线分析证明了新合成的化合物结构1 H，1313 C NMR光谱和元素分析。系统研究了这些染料的紫外可见吸收，发射，溶剂变色，溶剂荧光变色，氧化还原性质以及热稳定性和量子化学计算，以概述结构与性质之间的关系。这些染料在200°C以上具有适度的热分解温度，无显着的溶剂变色现象，正，显着的溶剂变色现象，较大的斯托克斯频移和绿色，黄色，橙色和红色发光，在非极性溶剂和稀溶液中的量子产率范围为0.03至0.93。电影。 量子化学计算（DFT）显示，所有染料均在2.77至3.22 eV之间显示出小的HOMO / LUMO缺口，这与实验数据相符。
• Synthesis of 1,1,3-Trisubstituted Naphtho[2,3-c]pyran-5,10-dione Derivatives as Potential Redox Switches
  作者：Tien-Lan Shie、Chi-Hui Lin、Shih-Lun Lin、Ding-Yah Yang

  DOI：10.1002/ejoc.200700426

  日期：2007.10

  Five 1,1,3-trisubstituted naphtho[2,3-c]pyran-5,10-dione derivatives were designed and synthesized in five steps from 2-acetyl-1,3-indandione. Prepared quinones 6a–e instantly changed from either red or blue to yellow or orange red, when treated with sodium borohydride in methanol. The resulting reduced hydroquinones 9a–e reverted to their original colors within a few minutes after the reducing agent

  五个 1,1,3-三取代的萘并 [2,3-c] 吡喃-5,10-二酮衍生物被设计和合成在五个步骤中从 2-乙酰基-1,3-茚满二酮。当用甲醇中的硼氢化钠处理时，制备的醌 6a-e 立即从红色或蓝色变为黄色或橙红色。在还原剂被消耗或去除后的几分钟内，生成的还原氢醌 9a-e 恢复到原来的颜色。虽然在还原之前没有检测到蓝色醌 6e 的荧光，但还原的氢醌 9e 发出红色荧光，量子产率为 0.07。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2007）
• Structure, reactivity, and application of some triketone derivatives
  作者：You-Sheng Chen、Pei-Yu Kuo、Tien-Lan Shie、Ding-Yah Yang

  DOI：10.1016/j.tet.2006.07.053

  日期：2006.10

  The major tautomer of several triketone derivatives in organic and aqueous solutions has been determined. Their solvent- and base-sensitive properties have been applied in the design of a polarity-sensitive fluorescent probe and an acidichromic colorant, respectively. The regioselective acetylation and methylation of 2-acyldimedone, 3-acyl-4-hydroxycoumarin, and 2-acyl-1,3-indandione have also been

  已经确定了有机和水溶液中几种三酮衍生物的主要互变异构体。它们对溶剂和碱的敏感特性已分别应用于极性敏感的荧光探针和酸性变色着色剂的设计中。还研究了2-酰基二酮，3-酰基-4-羟基香豆素和2-酰基-1,3-茚满二酮的区域选择性乙酰化和甲基化。结果表明，前两个的乙酰化和甲基化特别发生在环内烯醇氧处，而对于后者，它们发生在环外的烯醇氧处。
• Synthesis, optical and electrochemical properties of substituted 2-cinnamoyl-1, 3-indandione O-methyl ethers
  作者：Ilze Malina、Valdis Kampars、Baiba Turovska

  DOI：10.1016/j.molstruc.2016.02.090

  日期：2016.7

  Seven new 2-cinnamoyl-1,3-indandione (2CID) O-methyl ethers with different substituents (R = -H, -CH3, -OCH3, -N(C6H5)(2), -N(CH2CH2CN)(2), julolidyl, -N(CH3)(2)) in 4-position of the cinnamoyl moiety were synthesized. The methylation with dimethylsulfate occurred at the oxygen atom of the exocyclic enol group with high selectivity.The synthesized compounds were characterized by H-1, C-13 NMR, IR, UV-Vis and luminescence spectroscopy, their electrochemical properties were investigated by cyclic voltammetry. The obtained results indicates that introducing an electron donating substituents in the 4-position of cinnamoyl moiety facilitates electrochemical oxidation, remarkably shifts absorption and emission bands to longer wavelengths, simultaneously increases extinction coefficient (epsilon). O-methyl ethers with strong electron donating groups (R = -N(C6H5)(2), -N(CH2CH2CN)(2), julolidyl, -N(CH3)(2)) in molecule are characterized by luminescence with maximum in range from 547 to 647 nm and absolute photoluminescence quantum yields from 0.02 to 0.32. Quantum yield (QY) of chromophore containing julolidyl fragment is solvent dependent. It was 0.32 in chloroform and decreased in other polar (ethanol, acetone) solvents. (C) 2016 Elsevier B.V. All rights reserved.
• Quantum chemical and spectroscopic study of the structure of 2-acetylindan-1,3-dione complexes with metal(II) ions
  作者：Venelin Enchev、Anife Ahmedova、Galya Ivanova、Iwona Wawer、Neyko Stoyanov、Mariana Mitewa

  DOI：10.1016/s0022-2860(01)00522-1

  日期：2001.9

  A series of M(II) (M = Cu, Zn, Cd, Pb) complexes with the physiologically active 2-acetylindan-1,3-dione were synthesized. All complexes were obtained with the metal to ligand ratio 1:2. The presence of two water molecules in the inner coordination sphere of the Zn(II) and Cd(H) complexes was proven. The structure and coordination mode of the newly synthesized Cd(H) and Pb(II) complexes were investigated using NMR (C-13 CPMAS and C-13 NMR in DMF-d(7) solution) method. Semi-empirical (PM3) and ab initio (ECP-31G) calculations of the structure and IR spectra of the free ligand and corresponding metal(II) complexes were performed. It is shown that the structure of the Pb(II) complex differs significantly from the distorted tetrahedral structure of the Cu(II), Zn(II) and Cd(II) complexes. (C) 2001 Elsevier Science B.V. All rights reserved.