甲基 3-氰基-2-羟基-6-甲基异尼古丁酸酯 | 18724-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 甲基 3-氰基-2-羟基-6-甲基异尼古丁酸酯
• 中文别名: 甲基3-氰基-2-羟基-6-甲基异尼古丁酸酯
• 英文名称: methyl 6-methyl-2-oxo-3-cyano-1,2-dihydropyridine-4-carboxylate
• 英文别名: Methyl 3-cyano-6-methyl-2-pyridone-4-carboxylate；2-Oxo-6-methyl-3-cyan-1,2-dihydro-isonicotinsaeure-methylester；5-Cyano-2-methyl-pyrid-6-on-4-carbonsaeuremethylester；methyl 3-cyano-6-methyl-2-oxo-1H-pyridine-4-carboxylate
• CAS: 18724-73-7
• 化学式: C₉H₈N₂O₃
• mdl: MFCD15146655
• 分子量: 192.174
• InChiKey: MGPAFDWANYPSBL-UHFFFAOYSA-N

物化性质

• 熔点：
  227-230 °C
• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  甲基 3-氰基-2-羟基-6-甲基异尼古丁酸酯 在 硫酸 作用下， 反应 0.02h， 以87%的产率得到6-甲基-5H-吡咯并[3,4-c]吡啶-1,3,4-三酮
  参考文献：
  名称：

  Alkyl 2-amino-5,6-dialkyl-3-cyanopyridine-4-carboxylates in reactions with electrophilic reagents

  摘要：

  In reaction of alkyl 2-amino-5,6-dialkyl-3-cyanopyridine-4-carboxylates with isocyanates formed unstable ureas, and with nitrous acid at 60-70 C alkyl 5,6-dialkyl-2-oxo-1,2-dihydro-4-pyidinecarboxylates were obtained. It was shown for the latter that their reactions with organic acids and amides occurred at the cyano group, and the alkaline hydrolysis involved the ester group.

  DOI：

  10.1134/s1070428007100223
• 作为产物：
  描述：

  甲基2-氨基-3-氰基-6-甲基异烟酸酯 在 sodium nitrite 作用下， 以 水 为溶剂， 以38%的产率得到甲基 3-氰基-2-羟基-6-甲基异尼古丁酸酯
  参考文献：
  名称：

  Alkyl 2-amino-5,6-dialkyl-3-cyanopyridine-4-carboxylates in reactions with electrophilic reagents

  摘要：

  In reaction of alkyl 2-amino-5,6-dialkyl-3-cyanopyridine-4-carboxylates with isocyanates formed unstable ureas, and with nitrous acid at 60-70 C alkyl 5,6-dialkyl-2-oxo-1,2-dihydro-4-pyidinecarboxylates were obtained. It was shown for the latter that their reactions with organic acids and amides occurred at the cyano group, and the alkaline hydrolysis involved the ester group.

  DOI：

  10.1134/s1070428007100223

文献信息

• Effect of a Substituent in the Fourth Position on the Optical Properties of 2-Oxonicotinonitriles
  作者：S. P. Sorokin、S. V. Fedoseev、O. V. Ershov

  DOI：10.1134/s1070363222110366

  日期：2022.11

  Based on six representatives of 2-oxonicotinonitriles, the effect of the nature of the substituent in the fourth position of the pyridine system on the photophysical characteristics was studied. The role of the donor/acceptor nature of the substituent and the solvent nature in the absorbing and fluorescent properties of the compounds was shown.

  以六种代表的2-氧代烟腈为基础，研究了吡啶体系第四位取代基的性质对光物理特性的影响。显示了取代基的供体/受体性质和溶剂性质在化合物的吸收和荧光性质中的作用。
• The Synthesis of 6-Chloropyridoxine. The Hydride Reduction of Pyridinedicarboxylic Acids
  作者：Robert K. Blackwood、Glenn B. Hess、Clifford E. Larrabee、Frederick J. Pilgrim

  DOI：10.1021/ja01556a021

  日期：1958.12
• Practical and Scalable Synthesis of S1P₁ Receptor Agonist ACT-209905
  作者：Gunther Schmidt、Stefan Reber、Martin H. Bolli、Stefan Abele

  DOI：10.1021/op200326s

  日期：2012.4.20

  A practical and scalable route for the fast delivery of 12 kg of S1P(1) agonist (ACT-209905) has been developed. ACT-209905 is composed of an amino pyridine group, an oxadiazole spacer, a 2-ethyl-5-methylphenol moiety and a chiral 1-amino-2-propanol side chain. The convergent synthesis consists of 16 steps with 9 isolated intermediates and is chromatography-free. Key building blocks are accessed from low-cost starting materials, such as acetone, diethyl oxalate, cyanoacetamide, and 2-ethyl-5-methyl aniline. A Negishi coupling that was troubled by the use of metal reagents and concomitant metal waste streams has been replaced by a less expensive Guareschi-Thorpe reaction to build up an amino isonicotinic acid. The chiral 1-amino-2-propanol moiety was secured by selective ring-opening of an epoxide with lithium hexamethyldisilazide as an ammonia surrogate, thus omitting the notorious double alkylated byproduct.
• STOUT, D. M.;JAMAMOTO, D. M.;BARSELON-JANG, C.
  作者：STOUT, D. M.、JAMAMOTO, D. M.、BARSELON-JANG, C.

  DOI：——

  日期：——
• YOSHIDA KEA; OTOMASU HIROTAKA, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. <YKKZ-AJ>, 1976, 96+
  作者：YOSHIDA KEA、 OTOMASU HIROTAKA

  DOI：——

  日期：——