1-acetyl-5-methoxyisatin | 118726-73-1

• 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
• 英文名称: 1-acetyl-5-methoxyisatin
• 英文别名: 1-acetyl-5-methoxyindoline-2,3-dione；1-Acetyl-5-methoxy-indolin-2,3-dion；1-Acetyl-5-methoxy-2,3-dihydro-1H-indole-2,3-dione；1-acetyl-5-methoxyindole-2,3-dione
• CAS: 118726-73-1
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: JURGADAWMSUMID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-acetyl-5-methoxyisatin 在 C₃₂H₂₈F₆N₄O₃ 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-5-methoxy-4’-(2-oxo-1-phenylethyl)-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]
  参考文献：
  名称：

  基于Cinchona的方酰胺催化的级联氮杂-迈克尔-迈克尔加成反应：对映选择性的功能化螺氧基吲哚四氢喹啉的构建。

  摘要：

  已开发出一种有效的对映选择性级联氮杂-迈克尔-迈克尔加成反应，该反应由手性双官能叔胺-方酸酰胺催化剂催化。该级联反应在温和条件下进行得很好，提供了具有三个连续立体中心的高度官能化的螺并吲哚四氢喹啉，并具有优异的收率，出色的非对映选择性（> 25：1 dr）和高对映选择性（高达94％ee）。

  DOI：

  10.1039/c3cc44930k
• 作为产物：
  描述：

  5-甲氧基靛红 、 乙酸酐 反应 5.0h， 生成 1-acetyl-5-methoxyisatin
  参考文献：
  名称：

  通过硫脲催化的不对称Michael-Henry级联反应构建高度对映体富集的包含四个连续立体中心的螺环戊烷吲哚。

  摘要：

  以简单的3-取代的羟吲哚和硝基乙烯基乙酰胺为起始原料，成功实现了硫脲催化不对称合成高度手性富集的含有手性酰胺官能团的螺环戊烷氧吲哚。该方案具有操作简便，原子经济性高和催化不对称性高的特点，因此代表了一种通用的方法，用于合成高度对映体富集的螺环戊烷并吲哚。

  DOI：

  10.3762/bjoc.13.131

文献信息

• Diastereo- and Enantioselective Construction of Dihydroisocoumarin-Based Spirooxindole Frameworks <i>via</i> Organocatalytic Tandem Reactions
  作者：Jia-Le Wu、Bai-Xiang Du、Yu-Chen Zhang、Ying-Ying He、Jing-Yi Wang、Ping Wu、Feng Shi

  DOI：10.1002/adsc.201600271

  日期：2016.9.1

  An organocatalytic asymmetric approach has been developed for the ennantioselective construction of dihydroisocoumarin‐based spirooxindole frameworks in high yields, excellent diastereo‐ and enantioselectivities (up to 99%, all >95:5 dr, up to 99% ee). This approach takes advantage of chiral thiourea‐tertiaryamine catalyzed tandem reaction of isatins with enolizable homophthalic anhydride, which has

  已开发出一种有机催化不对称方法，用于高产率，出色的非对映异构和对映选择性（高达99％，所有> 95：5 dr，高达99％ee）的基于二氢异香豆素的螺并恶臭吲哚骨架的天线选择性构建。这种方法利用了手性硫脲-叔胺催化的靛红与可烯醇化的邻苯二甲酸酐的串联反应，该反应具有广泛的底物范围，并且可以在低催化剂负载下进行。该反应不仅为构建对映体富集的基于二氢异香豆素的螺氧杂吲哚骨架提供了一种有效而有用的方法，而且还将丰富催化重要的不对称串联反应和对映体选择性合成重要的螺环辛多酚的研究内容。
• 一种基于烯丙基硫叶立德作为三碳合成子的氧化吲哚螺环化合物及其合成方法
  申请人：天津理工大学

  公开号：CN107337631A

  公开（公告）日：2017-11-10

  一种基于烯丙基硫叶立德作为三碳合成子的氧化吲哚螺环化合物，其化学分子通式为C21+mH21+nO6+x，其中m,n,x均为1‑10的整数，且分子具有以下结构其中：R1为甲基、乙基、乙酰基、甲基乙基醚、苄基或二碳酸二叔丁基；R2为羟基、甲氧基或乙氧基；R3为5‑F、5‑Br、5‑Cl、5‑CH3、5‑O 、6‑Cl、6‑Br、6‑O 、7‑ 、7‑Cl或7‑Br。本发明的优点是：该方法利用串联反应的特性，达到一步合成目标产物的目的，显著的提高了反应效率、节省反应时间、简化反应步骤，为三取代的五元氧化螺环化合物提供了一个全新的方法和思路，对类似化合物的合成具有一定的参考价值。
• Synthesis of 5H-Pyrazino[2,3-b]indoles from Indole-2,3-dione Derivatives.
  作者：Jan Bergman、Hans Vallberg、Per-Ola Norrby、Björn Åkermark、Ward T. Robinson、Bryan R. Wood、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0742

  日期：——

  Reaction of N-acetylindol-2,3-diones with ethylenediamines gave the dihydro-pyrazinones 11, which could, after dehydrogenation and deacetylation be transformed to the corresponding 5H-pyrazino[2,3-b]indoles 5. N,N-Dimethylaminoethylation of the anion of 5 occurred selectively in the 5-position. Thermolysis of 1-pyrazinylbenzotriazole gave pyrazino[1,2-a]-benzimidazole 33 and no 5H-pyrazino[2,3-b] indole.
• Diverse synthesis of pyrano[2,3-b]indol and dihydropyrano[2,3-b]indol via tunable Lewis bases catalyzed domino reactions
  作者：Yufen Liu、Yanlong Du、Aimin Yu、Dabin Qin、Xiangtai Meng

  DOI：10.1016/j.tet.2015.07.057

  日期：2015.10

  We first reported an example of diverse synthesis of pyrano[2,3-b]indol and dihydropyrano[2,3-b]indol from the same starting materials. In these domino reactions, we can control the reaction conditions to give three new products: pyrano[2,3-b]indol, dihydropyrano[2,3-b]indol with E or Z exocyclic double bond. Using DABCO as catalyst in THF, dihydropyrano[2,3-b]indol with E exocyclic double bond and pyrano[2,3-b]indol were obtained at room temperature and 65 degrees C, respectively. In contrast, when DMAP was selected as catalyst, dihydropyrano[2,3-b]indol with Z exocyclic double bond was formed in toluene at 80 degrees C. (C) 2015 Elsevier Ltd. All rights reserved.
• New hydrazides derivatives of isoniazid against Mycobacterium tuberculosis: Higher potency and lower hepatocytotoxicity
  作者：Frederico Silva Castelo-Branco、Evanoel Crizanto de Lima、Jorge Luiz de Oliveira Domingos、Angelo C. Pinto、Maria Cristina S. Lourenço、Karen Machado Gomes、Mariana Marques Costa-Lima、Carlos Fernando Araujo-Lima、Claudia Alessandra Fortes Aiub、Israel Felzenszwalb、Thadeu Estevam M.M. Costa、Carmen Penido、Maria G. Henriques、Nubia Boechat

  DOI：10.1016/j.ejmech.2018.01.071

  日期：2018.2

  Tuberculosis (TB) is one of the leading causes of death worldwide. The emergence of multi-drug resistant strains of Mycobacterium tuberculosis (Mtb) and TB-HIV co-infection are major public health challenges. The anti-TB drugs of first choice were developed more than 4 decades ago and present several adverse effects, making the treatment of TB even more complicated and the development of new chemotherapeutics for this disease imperative. In this work, we synthesized two series of new acylhydrazides and evaluated their activity against different strains of Mtb. Derivatives of isoniazid (INH) showed important anti-Mtb activity, some being more potent than all anti-TB drugs of first choice. Moreover, three compounds proved to be more potent than INH against resistant Mtb. The Ames test showed favorable results for two of these substances compared to INH, one of which presented expressly lower toxicity to HepG2 cells than that of INH. This result shows that this compound has the potential to overcome one of the main adverse effects of this drug. (C) 2018 Elsevier Masson SAS. All rights reserved.