3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline | 53700-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline
• 英文别名: methyl (2Z)-2-(3-oxo-1,4-dihydroquinoxalin-2-ylidene)acetate
• CAS: 53700-46-2
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: JHBSHCXBAZNMSM-TWGQIWQCSA-N

物化性质

• 熔点：
  >227 °C (decomp)
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 4-bromo-3-methoxcarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  Kurasawa, Yoshihisa; Takada, Atsushi, Heterocycles, 1983, vol. 20, # 1, p. 121

  摘要：

  DOI：
• 作为产物：
  描述：

  4-chloro-3-(1-chloro-1-methoxcarbonyl)methylene-2-oxo-1,2,3,4-tetrahydroquinoxaline 在 zinc(II) iodide 作用下， 以 溶剂黄146 、 三氟乙酸 为溶剂， 反应 6.0h， 以57.7%的产率得到3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  Kurasawa, Yoshihisa; Moritaki, Yujiro; Ichikawa, Mitsugo, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 9, p. 3009 - 3013

  摘要：

  DOI：

文献信息

• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• Addition reactions of heterocyclic compounds. Part 74. Products from dimethyl acetylenedicarboxylate with thiourea, thioamide, and guanidine derivatives
  作者：R. Morrin Acheson、John D. Wallis

  DOI：10.1039/p19810000415

  日期：——

  in acetonitrile gave a fused thiazolidinone derivative, but in methanol a fused thiazinone was obtained. Structures were assigned to adducts from other thioureas by comparison with the 13C n.m.r. spectra for these compounds. A method has been developed for distinguishing between the possible structural types of adducts for guanidine and amidine derivatives with DMAD using 1H and 13C n.m.r. spectroscopy

  将苯并咪唑-2-硫酮与乙炔二甲酸二甲酯（DMAD）在乙腈中混合，得到稠合的噻唑烷酮衍生物，但在甲醇中，得到了稠合的噻嗪酮。通过与这些化合物的13 C nmr光谱比较，将结构分配给其他硫脲的加合物。已开发出一种使用1 H和13 C nmr光谱技术来区分DMAD与胍和am衍生物的加合物可能的结构类型的方法。从各种硫代酰胺和DMAD的产物通过其核磁共振谱和其他光谱进行鉴定。
• Hydroamination Reactions of Alkynes with<i>ortho</i>-Substituted Anilines in Ball Mills: Synthesis of Benzannulated N-Heterocycles by a Cascade Reaction
  作者：Maik Weiße、Markus Zille、Katharina Jacob、Robert Schmidt、Achim Stolle

  DOI：10.1002/chem.201406306

  日期：2015.4.20

  electrophilic alkynes and anilines with OH, NH, or SH groups in the ortho position. For the heterocycle formation, it was shown that several stress conditions were able to initiate the reaction in the solid state. Processing in a ball mill seemed to be advantageous over comminution with mortar and pestle with respect to process control. In the latter case, significant postreaction modification occurred during

  结果表明，在行星式球磨机中，邻位取代的苯胺易于与乙炔二羧酸二乙酯发生加氢胺化反应。分子间加氢反应与分子内闭环的顺序偶联被用于由易得的结构单元即邻位具有OH，NH或SH基团的亲电炔烃和苯胺合成苯并恶嗪，喹喔啉和苯并噻嗪位置。对于杂环的形成，已表明几种应力条件能够以固态引发反应。就过程控制而言，在球磨机中进行处理似乎比用研钵和研杵粉碎更为有利。在后一种情况下，固态分析期间发生了显着的反应后修饰。低温研磨证明对试剂的分子转化有不利影响。
• Synthesis and reactions of 3-(1,3,4-oxadiazol-2-yl)methylene-2-oxo-1,2,3,4-tetrahydroquinoxalines.
  作者：YOSHIHISA KURASAWA、YUJIRO MORITAKI、TERUMI EBUKURO、ATSUSHI TAKADA

  DOI：10.1248/cpb.31.3897

  日期：——

  Various 3-(1, 3, 4-oxadiazol-2-yl) methylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (4a, 4b, 5a, 5b, and 6) were prepared from 3-methoxycarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline (1) via 3-hydrazinocarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline (2) and 3-(substituted hydrazino) carbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (3a and 3b). Compound 3a was also cyclized to 1, 2-dihydro-2-oxo-3-(5-oxo-3-pyrazolin-4-yl) quinoxaline (7).

  4-四氢喹喔啉（1）通过 3-肼基羰基亚甲基-2-氧代-1，2，3，4-四氢喹喔啉（2）和 3-（取代的肼）羰基亚甲基-2-氧代-1，2，3，4-四氢喹喔啉（3a 和 3b）制备而成。化合物 3a 还环化成 1，2-二氢-2-氧代-3-(5-氧代-3-吡唑啉-4-基)喹喔啉（7）。
• ¹H-NMR study on the tautomer ratios between the hydrazone imine and diazenylenamine forms in 3-(arylhydrazono)-methyl-2-oxo-1,2-dihydroquinoxalines
  作者：Yoshihisa Kurasawa、Akiko Takano、Kyoko Kato、Atsushi Takada、Ho Sik Kim、Yoshihisa Okamoto

  DOI：10.1002/jhet.5570330234

  日期：1996.3

  o-substituted 3-(arylhydrazono)methyl-2-oxo-1,2-dihydroquinoxalines 1a-c and 2a, c were synthesized to investigate the tautomeric behavior between the hydrazone imine A and diazenylenamine B forms in a series of mixed dimethyl sulfoxide/trifluoroacetic acid media. The chemical shifts of the hydrazone NH, N4-H, hydrazone CH, and diazenyl CH protons for o-, m-, and p-substituted 3-(arylhydrazono)methyl-2-oxo-1

  所述Ô取代3-（芳基亚肼基）甲基-2-氧代-1,2- dihydroquinoxalines 1A-1C和图2A，C合成调查腙亚胺之间的互变异构行为甲和diazenylenamine乙一系列混合二甲基亚砜形式/三氟乙酸介质。o NH，N 4 -H，CH和重氮烯基CH质子对o-，m-和p-取代的3-（芳基azo基）甲基-2-氧代-1,2-二氢喹喔啉1和2的化学位移迄今合成的化合物分别总结在表3和表4中，由于to亚胺形式A（hydr NH，CH CH）和重氮烯基胺形式B（N 4 -H，二氮烯基CH）。