3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione | 6011-63-8

• 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
• 英文名称: 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione
• 英文别名: 3-hydroxy-[3,3'-biindoline]-2,2'-dione；3-hydroxy-(3,3’-biindoline)-2,2’-dione；Isatan；3-hydroxy-3-(2-oxo-1,3-dihydroindol-3-yl)-1H-indol-2-one
• CAS: 6011-63-8
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: UICXCEVTIDQFDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 [3,3'-biindoline]-2,2'-dione
  参考文献：
  名称：

  Marschalk, Bulletin de la Societe Chimique de France, 1952, p. 949

  摘要：

  DOI：
• 作为产物：
  描述：

  1H,1H'-2,2'-Biindolylidene-3,3'-dione 在 硫化氢铵 、 铬酸 作用下， 生成 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione
  参考文献：
  名称：

  Erdmann, Journal fur praktische Chemie (Leipzig 1954), 1841, vol. <1>24, p. 15

  摘要：

  DOI：

文献信息

• Iron‐Catalyzed Direct Oxidative Alkylation and Hydroxylation of Indolin‐2‐ones with Alkyl‐Substituted N‐Heteroarenes
  作者：Ren‐Ming Hu、Dong‐Yang Han、Ning Li、Jie Huang、Yu Feng、Da‐Zhen Xu

  DOI：10.1002/anie.201913400

  日期：2020.3.2

  alkyl-substituted N-heteroarenes, through an oxidative cross-coupling reaction. The reaction is catalyzed by a simple iron salt under mild ligand-free and base-free conditions. The reaction is environmentally benign, employs air (molecular oxygen) as the terminal oxidant and oxygen source for the synthesis of O-containing compounds, and produces only water as the byproduct.

  本文提出的是两个不同的C（sp3）-H键，吲哚-2-酮和烷基取代的N-杂芳烃之间通过氧化交叉偶联反应的首次直接烷基化和羟基化反应。该反应由简单的铁盐在温和的无配体和无碱条件下催化。该反应在环境上是无害的，使用空气（分子氧）作为末端氧化剂和氧源来合成含O的化合物，仅产生水作为副产物。
• “On water” catalyst-free, column chromatography-free and atom economical protocol for highly diastereoselective synthesis of novel class of 3-substituted, 3-hydroxy-2-oxindole scaffolds at room temperature
  作者：Pramod B. Thakur、Harshadas M. Meshram

  DOI：10.1039/c3ra46271d

  日期：——

  The “on water” highly atom economical and diastereoselective synthesis of a novel class of 3-(thiazolidinedione or oxindole) substituted, 3-hydroxy-2-oxindole scaffolds has been achieved by the reaction of isatin electrophiles with thiazolidinedione or oxindole nucleophiles in a catalyst-free and column chromatography-free protocol at room temperature. The generality of the method has been demonstrated by screening a series of isatin electrophiles as well as thiazolidinedione and oxindole derivatives. The developed method is one of the rare examples of an ideal green protocol for the synthesis of medicinally important 3-hydroxy-2-oxindole scaffolds in which the straightforward synthesis of such a framework was achieved by employing very mild, simple and handy procedures from readily available starting materials.

  通过在室温下使用无催化剂和无柱层析的协议，实现了一类新型3-(噻唑烷二酮或羟吲哚)取代的、3-羟基-2-羟吲哚骨架的“在水相中”高原子经济性和高对映选择性合成，这是通过二酮亚胺电子供体与噻唑烷二酮或羟吲哚亲核试剂的反应实现的。该方法的普遍性已通过筛选一系列二酮亚胺电子供体以及噻唑烷二酮和羟吲哚衍生物得到证明。所开发的方法是少数理想绿色合成方案的例子之一，用于合成医药上重要的3-羟基-2-羟吲哚骨架，其中通过采用非常温和、简单且便捷的操作从易于获得的起始材料中实现了这种框架的直接合成。
• 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel–Crafts alkylation reactions in aqueous medium
  作者：Sakkani Nagaraju、Kota Sathish、Banoth Paplal、Neeli Satyanarayana、Dhurke Kashinath

  DOI：10.1039/c9nj03209f

  日期：——

  retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used for the selective synthesis of 3-hydroxy-indolyl-2-oxindoles and bis-indolyl-2-oxindoles (symmetric/unsymmetric) via retro-Henry type reaction followed by Friedel–Crafts alkylation

  复古亨利型反应的第一示例是使用报道3-羟基-3 - （（3-甲基-4- nitroisoxazol -5-基）甲基），其制备二氢吲哚-2-酮通过的不含催化剂的亨利反应3,5-二甲基-4-硝基异恶唑和靛红。这些化合物用于通过逆亨利型反应，然后在水中进行Friedel-Crafts烷基化反应（一锅法）选择性合成3-羟基-吲哚基-2-氧吲哚和双吲哚基-2-氧吲哚（对称/不对称）。方法）。3-羟基-3-（（3-甲基-4-硝基异恶唑-5-基）甲基）吲哚-2-酮在水解后生成2-（3-羟基-2-氧代吲哚-3-基）乙酸，为天然产物和生物活性化合物的来源。
• Catalytic activity of nickel(II), copper(II) and oxovanadium(II)-dihydroindolone complexes towards homogeneous oxidation reactions
  作者：Mohamed Shaker S. Adam

  DOI：10.1002/aoc.4234

  日期：2018.4

  molar ratios. A comparison in the catalytic potential of paramagnetic complexes of low and high valent metal ion was explored in the oxidation processes of cis‐cyclooctene, benzyl alcohol and thiophene by an aqueous H2O2, as a green terminal oxidant, in the presence and absence of acetonitrile, as an organic solvent, at 85 °C. NiH2ID, CuH2ID and VOH2ID show good catalytic activity, i.e. good chemo‐ and

  合成了3种新颖的Ni 2 +，Cu 2+和VO 2+离子与3-羟基-3,3'-二吲哚啉-2,2'-二酮（二氢吲哚酮，H 4 ID）的顺磁性金属配合物（MH 2 ID）并具有不同的光谱学方法。通过在甲醇中苯丙氨酸存在下，靛红的均偶联反应合成配体（H 4 ID）。低价Ni 2 +，Cu 2+离子和高价VO 2+离子与H 4的络合内径以1：2的摩尔比进行。在存在和不存在下，在H 2 O 2作为绿色末端氧化剂的条件下，顺式-环辛烯，苄醇和噻吩在顺式-环辛烯，苄醇和噻吩的氧化过程中，对低和高价金属离子的顺磁性配合物的催化潜力进行了比较在85°C下乙腈作为有机溶剂。NiH 2 ID，CuH 2 ID和VOH 2 ID显示出良好的催化活性，即良好的化学和区域选择性。与Ni 2 + -和Cu 2+相比，VOH 2 ID具有最高的催化潜力-在相同的均匀好氧气氛中进行种。还使用NiH 2 ID，CuH 2 ID或VOH
• Efficient green synthesis of isoindigo derivatives using sulfonic-acid-functionalized nanoporous silica (SBA-Pr-SO3H) catalyst and study of their antimicrobial properties
  作者：Parisa Gholamzadeh、Ghodsi Mohammadi Ziarani、Alireza Badiei、Ali Abolhassani Soorki、Negar Lashgari

  DOI：10.1007/s11164-012-0909-y

  日期：2013.11

  An efficient green condensation reaction has been developed for synthesis of trans-isoindigo derivatives using SBA-Pr-SO3H with pore size of 6 nm as a heterogeneous nanoporous acid catalyst under solvent-free conditions. Isoindigo derivatives have many industrial applications, e.g., dyes, drugs, organic solar cells, and semiconductor memories. The antimicrobial activities of these compounds have also been tested.

  已开发出一种高效的绿色缩合反应，使用孔径为6纳米的SBA-Pr-SO3H作为异质纳米孔酸催化剂，在无溶剂条件下合成trans-异苯骈二氮杂环衍生物。异苯骈二氮杂环衍生物在染料、药物、有机太阳能电池和半导体存储等多个工业领域有广泛应用。这些化合物的抗菌活性也进行了测试。