3-硝基噻吩-2-羧酸甲酯 | 75735-44-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-硝基噻吩-2-羧酸甲酯
• 英文名称: Methyl 3-nitrothiophene-2-carboxylate
• 英文别名: 3-nitro-2-methoxycarbonylthiophen；3-nitro-thiophene-2-carboxylic acid methyl ester；3-Nitro-thiophen-2-carbonsaeure-methylester；3-nitrothiophene-2-carboxylic acid methyl ester
• CAS: 75735-44-3
• 化学式: C₆H₅NO₄S
• mdl: MFCD15143335
• 分子量: 187.176
• InChiKey: DDLFZCCIZTVFBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  299.4±20.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-硝基噻吩-2-羧酸甲酯 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 5-溴-3-硝基噻吩-2-羧酸
  参考文献：
  名称：

  NOVEL 2,3,5-SUBSTITUTED THIOPHENE COMPOUND AS PROTEIN KINASE INHIBITOR

  摘要：

  公开号：

  EP3418275B1
• 作为产物：
  描述：

  3-氯磺酰基-2-噻吩甲酸甲酯 在 ammonium hydroxide 、 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 反应 1.34h， 生成 3-硝基噻吩-2-羧酸甲酯
  参考文献：
  名称：

  Transformation rates ofortho-substituted thiophene and benzene carboxylic esters: Application to thifensulfuron-methyl and metsulfuron-methyl herbicides

  摘要：

  AbstractThe rate constants for soil degradation and alkaline hydrolysis of two herbicides, metsulfuron‐methyl and thifensulfuron‐methyl, have been determined. In order to explain the difference in behaviour of the two compounds, the chemical and enzymatic hydrolysis of some ortho‐substituted methyl benzoates and methyl 3‐substituted thiophene‐2‐carboxylates were studied. The data are consistent with a difference in polar and steric effects of the substituents in benzene and thiophene derivatives.

  DOI：

  10.1002/ps.2780400407

文献信息

• ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS
  申请人：Gokaraju Ganga Raju

  公开号：US20100068178A1

  公开（公告）日：2010-03-18

  The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.

  本发明公开了一般式(I)和式(II)的三氮烯类似物，其互变异构体、立体异构体、多晶形态、水合物、溶剂合物及其在转移性恶性黑色素瘤和其他癌症，包括但不限于淋巴瘤、肉瘤、癌瘤和胶质瘤中的药用可接受盐。该发明还公开了制备上述式(I)和式(II)的三氮烯类似物以及其药用可接受组合物的方法。
• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• Factors controlling the selectivity of ipso-attack in homolytic aromatic substitutions. Reactions of alkyl radicals with nitrothiophen derivatives
  作者：Pietro Cogolli、Filippo Maiolo、Lorenzo Testaferri、Marcello Tiecco、Marco Tingoli

  DOI：10.1039/p29800001331

  日期：——

  The reactions of the nearly electroneutral methyl and of the nucleophilic 1-adamantyl radical with some selected nitrothiophen derivatives have been investigated in order to elucidate the factors which control the positional selectivity of radical addition to an aromatic substrate. With 5-nitro-2-X-thiophens (II), (V), and (VI) and 3,5-dinitro-2-methoxycarbonylthiophen (III) the adamantyl radical gave

  为了阐明控制自由基加成到芳族底物上的位置选择性的因素，已经研究了接近电子中性的甲基和亲核的1-金刚烷基与某些选定的硝基噻吩衍生物的反应。在具有5-硝基-2-X-噻吩（II），（V）和（VI）和3,5-二硝基-2-甲氧基羰基噻吩（III）的情况下，金刚烷基仅产生ipso攻击的产物，而甲基在未取代的4-位上有选择地添加一个残基。另一方面，带有4-硝基-2-甲氧基-羰基噻吩（I）的两个基团和带有4-5-二硝基-2-甲氧基羰基噻吩（IV）的两个基团均得到ipso的产物。-通过从5-位取代硝基来进行-取代。通过假定加成步骤的过渡态的性质根据自由基的极性特征和芳族底物的电子缺乏而变化来解释这些位置选择性的变化。
• Electrophilic Tetraalkylammonium Nitrate Nitration. II. Improved Anhydrous Aromatic and Heteroaromatic Mononitration with Tetramethylammonium Nitrate and Triflic Anhydride, Including Selected Microwave Examples
  作者：Scott A. Shackelford、Mark B. Anderson、Lance C. Christie、Thomas Goetzen、Mark C. Guzman、Martha A. Hananel、Wayne D. Kornreich、Haitao Li、Ved P. Pathak、Alex K. Rabinovich、Ranjan J. Rajapakse、Larry K. Truesdale、Stella M. Tsank、Haresh N. Vazir

  DOI：10.1021/jo026202q

  日期：2003.1.1

  A new one-pot nitration employing tetramethylammonium nitrate and trifluoromethanesulfonic anhydride in dichloromethane to provide a ready source of the nitronium triflate nitrating agent is presented. Rapid and selective nitration with a variety of aromatic and heteroaromatic substrates is achieved resulting in the synthesis of several novel organic compounds. A distinct advantage is the removal of

  提出了一种新的一锅式硝化方法，该方法采用硝酸四甲基铵和三氟甲磺酸酐在二氯甲烷中的溶液，以提供易于使用的三氟甲磺酸硝化硝化剂的来源。实现了多种芳香族和杂芳香族底物的快速选择性硝化，从而合成了几种新型有机化合物。一个明显的优点是通过水后处理除去不需要的副产物。这种非常温和的硝化作用可实现大规模合成，并获得较高的分离产物收率，而通常无需进一步纯化。这种基于硝酸四甲基铵的硝化也已应用于微波辅助条件，并概述了几种化合物的结果。
• An Easy Synthesis of 3-Amino- and 3-Nitrothiophene
  作者：John M. Barker、Patrick R. Huddleston、Michael L. Wood

  DOI：10.1080/00397919508011446

  日期：1995.12

  Abstract 3-Amino- and 3-nitrothiophene are readily made by the decarboxylation of the corresponding thiophene-2-carboxylic acids which are easily prepared from the commercially available methyl 3-aminothiophene-2-carboxylate.

  摘要 3-氨基-和3-硝基噻吩很容易通过相应的噻吩-2-羧酸脱羧来制备，而噻吩-2-羧酸很容易从市售的3-氨基噻吩-2-羧酸甲酯中制备。