2,2-dihydroxy-5-methyl-1H-indene-1,3(2H)-dione | 154458-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2-dihydroxy-5-methyl-1H-indene-1,3(2H)-dione
• 英文别名: 2,2-Dihydroxy-5-methylindene-1,3-dione
• CAS: 154458-11-4
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: YSFDBEXXZHVVAE-UHFFFAOYSA-N

物化性质

• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dihydroxy-5-methyl-1H-indene-1,3(2H)-dione 以 氯苯 为溶剂， 生成 5-methyl-1H-indene-1,2,3-trione
  参考文献：
  名称：

  Bowden, Keith; Rumpal, Sanjay, Journal of Chemical Research, Miniprint, 1997, # 2, p. 355 - 374

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基茚-1,3-二酮 在 溴 、 二甲基亚砜 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 5.0h， 生成 2,2-dihydroxy-5-methyl-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of some 11H-indeno[1,2-b]quinoxalin-11-ones

  摘要：

  Condensation of substituted o-phenylene diamines and ninhydrins gave the tide compounds. The substituent orientation in the products was determined by H-1 NMR analysis of the chemical shifts brought about by N5-oxidation. Reduction of the 8-nitro to 8-amino compound was achieved both with and without reduction of the carbonyl group. Nitration of the 8-carboxylic acid occurred in the 2-position.

  DOI：

  10.1016/s0040-4020(01)80184-8

文献信息

• Microwave-assisted oxidation of indan-1-ones into ninhydrins
  作者：Christelle Marminon、Abdelhamid Nacereddine、Zouhair Bouaziz、Pascal Nebois、Joachim Jose、Marc Le Borgne

  DOI：10.1016/j.tetlet.2015.02.086

  日期：2015.4

  A simple and general microwave-assisted selenium oxidation has been developed for the synthesis of substituted ninhydrins from indan-1-ones in order to access to indeno[1,2-b]indoles substituted on the A ring. This efficient and convenient oxidation, using selenium dioxide under microwave irradiations, afforded mono- and di-substituted ninhydrins in a single step reaction with good yields.

  已经开发了一种简单且通用的微波辅助硒氧化法，用于从茚满-1-酮合成取代的茚三酮，以便获得在A环上取代的茚并[1,2- b ]吲哚。在微波辐射下使用二氧化硒进行的这种有效且便捷的氧化反应，可在一步反应中以高收率得到单取代和二取代的茚三酮。
• Ninhydrins inhibit carbonic anhydrases directly binding to the metal ion
  作者：Abdeslem Bouzina、Malika Berredjem、Alessio Nocentini、Silvia Bua、Zouhair Bouaziz、Joachim Jose、Marc Le Borgne、Christelle Marminon、Paola Gratteri、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2020.112875

  日期：2021.1

  Ninhydrins show extensive application in organic chemistry and agriculture whereas they have been poorly investigated as bioactive molecules for medicinal chemistry purposes. A series of ninhydrin derivatives was here investigated for the inhibition of human carbonic anhydrases (CAs, EC 4.2.1.1), based on earlier evidence that gem diols are able to coordinate the metal ion from the CA active site.

  茚三酮在有机化学和农业中显示出广泛的应用，而作为药用化学目的，它们作为生物活性分子的研究很少。在此之前，根据宝石二醇能够协调CA活性位点上的金属离子的早期证据，研究了一系列茚三酮衍生物对人碳酸酐酶的抑制作用（CA，EC 4.2.1.1）。Ninhydrins显示出对CA I和IX（K微摩尔抑制作用我在范围0.57-68.2μM或多个）和高达针对CA II和VII纳摩尔效力（K我（范围为0.025-78.2μM），已验证的同工型可作为多种中枢神经系统相关疾病的靶标。相反，对CA IV的抑制作用较弱或较弱。使用基于对接，MM-GBSA和元动力学计算的计算方案来阐明这种抑制剂与CA II和CA VII的假定结合模式。这项研究的发现证明，这种药理学上被低估的配体可能代表了开发具有新颖作用机制（即通过二醇部分与锌离子单或双配位）的CA抑制剂的有趣的先导化合物。
• A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives
  作者：Kaki Raveendra Babu、Faiz Ahmed Khan

  DOI：10.1039/c4ob01977f

  日期：——

  isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal dihalo olefin moiety in the efficiently generated indenone derivatives was utilized to transform into ninhydrin derivatives by employing Ru(III)-catalyzed oxidation.

  报道了有效的酸诱导的四卤代7，7-二甲氧基双环[2.2.1]庚烯基系统的重排导致取代的茚满。该多米诺反应涉及脱水，烯烃异构化，缩酮水解，[3,3]-σ重排和脱卤化氢。通过Ru（III）催化的氧化，将有效生成的茚满酮衍生物中的所得邻位二卤代烯烃部分用于转化为茚三酮衍生物。
• Reactions of carbonyl compounds in basic solutions. Part 23.1 The mechanism of the base-catalysed ring fission of 2,2-dihydroxyindane-1,3-diones
  作者：Keith Bowden、Sanjay Rumpal

  DOI：10.1039/a606312h

  日期：——

  The base-catalysed ring fission of a series of substituted 2,2-dihydroxyindane-1,3-diones and phenalene-1,3-dione has been studied in 30% (v/v) dioxane–water. The reaction proceeds in two distinct steps. The first is a relatively fast base-catalysed ring fission to give substituted o-carboxyphenylglyoxals, and the second is a rearrangement of the latter resulting in formation of substituted o-carboxymandelic acids. Rate coefficients for the ring fission of a limited series of substrates have been determined at 25.0 °C. The reaction is first order in the mono-anion of the substrate alone. The Hammett reaction constants, ρ, have been obtained from both the kinetic and product studies. The rate- and product-determining step appears to be an intramolecular nucleophilic attack. The rate coefficients for the rearrangement have been determined for all substrates at 25.0, 35.0 and 45.0 °C. The activation parameters have been calculated. The kinetic solvent isotope, solvent and salt effects have been studied. The effects of the 5-substituted and 5,6-disubstituents on the rates have been correlated using a modified Hammett equation giving a reaction constant, ρ, equal to 3.4 at 25 °C.

  研究人员在 30% (v/v) 二噁烷-水中对一系列取代的 2,2-二羟基茚-1,3-二酮和苯丙烯-1,3-二酮进行了碱催化环裂变研究。反应分两个不同的步骤进行。第一步是相对较快的碱催化环裂变，生成取代的邻羧基苯基乙二醛；第二步是后者的重排，生成取代的邻羧基扁桃酸。在 25.0 °C条件下测定了一系列有限底物的环裂解速率系数。该反应仅在底物的单阴离子中为一阶反应。从动力学和产物研究中获得了哈米特反应常数 ρ。决定速率和产物的步骤似乎是分子内的亲核攻击。对所有底物在 25.0、35.0 和 45.0 °C 下的重排速率系数进行了测定。计算了活化参数。研究了动力学溶剂同位素、溶剂和盐的影响。使用改进的 Hammett 方程对 5 取代基和 5,6 二取代基对速率的影响进行了相关分析，得出 25 °C 时的反应常数 ρ 等于 3.4。
• Heteropolycyclic inhibitors of protein kinases
  申请人：——

  公开号：US20020035251A1

  公开（公告）日：2002-03-21

  A compound of the formula 1 wherein, independently at each occurrence, v, w, and x are selected from C, N, O, and S, with H substitution as needed to fulfill open valence sites; y and z are selected from N and C, with H substitution as needed to fulfill open valence sites, with the proviso that each of w, v, x, y and z is not simultaneously C; the ring formed from v, w, x, y and z may be saturated or unsaturated; and R 1 , R 2 , R 3 and R 4 are selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, heteroalkyl, and heteroaryl; wherein any adjacent two of R 1 , R 2 , R 3 and R 4 may join together to form a 5, 6 or 7-membered carbocyclic or heterocyclic ring, with the proviso that each of R 1 , R 2 , R 3 and R 4 is not simultaneously hydrogen. Pharmaceutical compositions of said compounds, and methods of use in the treatment of biological conditions including cellular hyperproliferation, are disclosed.

  该化合物的化学式为1，其中，在每个出现的v、w和x处，独立地选择C、N、O和S，必要时进行H取代以满足开放价位；y和z从N和C中选择，必要时进行H取代以满足开放价位，但w、v、x、y和z中的每个都不能同时为C；由v、w、x、y和z形成的环可以是饱和的或不饱和的；以及R1、R2、R3和R4从氢、烷基、芳基、烷芳基、芳基烷基、杂环烷基和杂环芳基中选择；其中，任何相邻的两个R1、R2、R3和R4都可以结合形成5、6或7成员的碳环或杂环，但R1、R2、R3和R4中的每个都不能同时为氢。还公开了该化合物的药物组合物以及在治疗包括细胞增殖过度在内的生物状况的方法。