2,3-二氧代二氢吲哚-4-羧酸甲酯 | 153072-43-6

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

2,3-二氧代二氢吲哚-4-羧酸甲酯

中文别名

——

英文名称

methyl 4-isatincarboxylate

英文别名

methyl 2,3-dioxo-2,3-dihydro-1H-indole-4-carboxylate；methyl 2,3-dioxoindoline-4-carboxylate；2,3-Dihydro-2,3-dioxo-1H-indole-4-carboxylic acid, methyl ester；methyl 2,3-dioxo-1H-indole-4-carboxylate

CAS

153072-43-6

化学式

C₁₀H₇NO₄

mdl

——

分子量

205.17

InChiKey

DKKOUROAVJVZRT-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.410±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.6
重原子数：

15
可旋转键数：

2
环数：

2.0
sp3杂化的碳原子比例：

0.1
拓扑面积：

72.5
氢给体数：

1
氢受体数：

4

安全信息

危险性防范说明：

P261,P305+P351+P338
危险性描述：

H302,H315,H319,H335
储存条件：

在无氧环境中，保存温度为2-8°C。

反应信息

作为反应物：

描述：

2,3-二氧代二氢吲哚-4-羧酸甲酯在硫酸、 sodium hydroxide 、 sodium azide 、异丙醇作用下，反应 0.34h，以93%的产率得到3-氨基邻苯二甲酰亚胺

参考文献：

名称：

酸催化合成 Isatoic Anhydride-8-Secondary 酰胺使 IASA 转化为药物化学

摘要：

喹唑啉二酮-N -3-烷基衍生物是几类生物活性小分子的核心支架，但目前的合成方法成本高，涉及环境危害，并且不能统一扩展。在这里，我们报告了一种廉价、灵活且可扩展的方法，用于从靛红中原位合成取代的喹唑啉-二酮-N -3-烷基（isatoic-8-仲酰胺 (IASAs) 的异构体）在酸性条件下捕获亚胺酸。我们进一步表明，该方法可用于合成多种具有药用用途的衍生物。

DOI：

10.1021/acs.joc.1c02036
作为产物：

描述：

3,3-dibromo-2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid methyl ester 在水作用下，以甲醇为溶剂，反应 4.0h，生成 2,3-二氧代二氢吲哚-4-羧酸甲酯

参考文献：

名称：

Structure-based design and parallel synthesis of N-benzyl isatin oximes as JNK3 MAP kinase inhibitors

摘要：

A series of N-benzylated isatin oximes were developed as inhibitors of the mitogen-activated kinase, JNK3. X-ray crystallographic structures aided in the design and synthesis of novel, selective compounds, that inhibit JNK3, but not p38 MAP kinase and provided key insights into understanding the behavior of gatekeeper residue methionine-146 in determining target selectivity for this series.

DOI：

10.1016/j.bmcl.2009.03.043

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文献信息

Palladium‐Catalyzed Cascade Hydrosilylation and Amino‐Methylation of Isatin Derivatives

作者：Yue Liu、Yun‐Tao Xia、Su‐Hang Cui、Yi‐Gang Ji、Lei Wu

DOI：10.1002/adsc.202000266

日期：2020.7.16

We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino‐methylation reaction can be realized. With DMF as a reactant and a solvent, the in‐situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N‐functionalized

我们证明，使用乙酸钯作为催化剂通过氢硅烷还原DMF和靛红衍生物，可以实现级联氢化硅烷化和氨基甲基化反应。用DMF作为反应物和溶剂，原位生成的甲硅烷氧基甲胺中间体（DMF和氢硅烷的加合物）顺利地参与了后续步骤，从而以中等至良好的收率提供了一系列Si，N-官能化的吲哚-2-酮。该策略在底物中表现出对羰基部分还原的高化学选择性。
Imino-Indeno[1,2-c] quinoline derivatives, their preparation processes, and pharmaceutical compositions comprising the same

申请人：Tzeng Cherng-Chyi

公开号：US20090111987A1

公开（公告）日：2009-04-30

Disclosed herein are novel imino-indeno[1,2-c]quinoline derivatives of formula (I): or a pharmaceutically acceptable salt or solvate thereof, wherein each of the substituents is given the definition as set forth in the Specification and Claims. Also disclosed are the preparation processes of these derivatives, their synthetic precursors and their uses in the manufacture of pharmaceutical compositions for use in the treatment of cancers.

本文披露了一种新型的imino-indeno[1,2-c]quinoline衍生物，其化学式为(I)：或其药用可接受的盐或溶剂，其中每个取代基的定义如规范和权利要求所述。还披露了这些衍生物的制备过程、它们的合成前体以及它们在制造用于治疗癌症的药物组合物中的用途。
GLYCINE TRANSPORTER INHIBITOR

申请人：TAISHO PHARMACEUTICAL CO., LTD.

公开号：US20160159814A1

公开（公告）日：2016-06-09

The present invention provides novel compounds of formula [I] or pharmaceutically acceptable salts thereof: which are useful in the prevention or treatment of diseases such as schizophrenia, Alzheimer's disease, cognitive impairment, dementia, anxiety disorders (e.g., generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, post-traumatic stress disorder, specific phobias, acute stress disorder), depression, drug dependence, spasm, tremor, pain, Parkinson's disease, attention deficit hyperactivity disorder, bipolar disorder, eating disorder, or sleep disorders, which is based on the glycine uptake-inhibiting action.

本发明提供了式[I]或其药学上可接受的盐的新化合物，其可用于预防或治疗诸如精神分裂症、阿尔茨海默病、认知障碍、痴呆、焦虑症（例如广泛性焦虑症、惊恐症、强迫症、社交性焦虑症、创伤后应激障碍、特定恐惧症、急性应激障碍）、抑郁症、药物依赖、痉挛、震颤、疼痛、帕金森病、注意力缺陷多动障碍、双相情感障碍、进食障碍或睡眠障碍等疾病，其基于甘氨酸摄取抑制作用。
ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

申请人：Universal Display Corporation

公开号：US20200291006A1

公开（公告）日：2020-09-17

Transition metal compounds having naphthalene imide moiety having enhanced electron withdrawing property and more metal-ligand charge transfer (MLCT) based excited state are disclosed. The disclosed compounds will improve the photoluminescent quantum yield (PLQY) and produce phosphorescent emission in red to near IR region which has many desired applications.

公开了具有萘二酰亚胺基团的过渡金属化合物，具有增强的电子提取性能和更多基于金属配体电荷转移（MLCT）的激发态。所公开的化合物将提高光致发光量子产率（PLQY）并在红至近红外区域产生磷光发射，具有许多理想的应用。
Domino Reactions Enable Zn-Mediated Direct Synthesis of Spiro-Fused 2-Oxindole-α-Methylene-γ-Butyrolactones/Lactams from Isatin Derivatives and 2-(Bromomethyl)acrylates

作者：Prathap Reddy Mukthapuram、Amarnath Natarajan

DOI：10.3390/molecules29153612

日期：——

are found in several biologically active molecules. Here, we report nucleophilic domino reactions for the synthesis of α-methylene-γ-butyrolactone/lactam containing spirocyclic oxindoles. The Zn-mediated one-step reaction accommodates a range of substrates and can be used to rapidly generate focused libraries of highly substituted spirocyclic compound.

在几种生物活性分子中发现了靛红衍生的螺环核心。在这里，我们报道了含有螺环羟吲哚的 α-亚甲基-γ-丁内酯/内酰胺合成的亲核多米诺反应。锌介导的一步反应适用于一系列底物，可用于快速生成高度取代的螺环化合物的集中库。