13490-32-9 4-氨基-N'-羟基-1,2,5-噁二唑-3-甲脒

中文名称: 4-氨基-N'-羟基-1,2,5-噁二唑-3-甲脒
英文名称: 4-Amino-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide
CAS号

词条详情加载中…

名称和标识

中文名: 4-氨基-N'-羟基-1,2,5-噁二唑-3-甲脒
英文名: 4-Amino-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide
CAS号: 13490-32-9
分子式: C3H5N5O2
分子量: 143.1
中文别名: 4-氨基-N-羟基-1,2,5-噁二唑-3-羧酰胺; 4-氨基-N'-羟基-1,2,5-恶二唑-3-甲酰亚胺酰胺; 4-氨基-N'-羟基-1,2,5-噁二唑-3-甲脒; 3-氨基-4-偕氨基肟基呋咱; 3-氨基-4-氨基肟基呋咱; 4-氨基-N-羟基-1,2,5-恶二唑-3-甲脒
英文别名: 4-AMINO-3-FURAZANECARBOXAMIDOXIME; 4-AMINO-N-HYDROXY-FURAZAN-3-CARBOXAMIDINE; 4-AMINO-N-HYDROXY-1,2,5-OXADIAZOLE-3-CARBOXIMIDAMIDE; 1,2,5-Oxadiazole-3-carboximidamide, 4-amino-N-hydroxy-

物化属性

Log S (Ali): -1.54
Log S (ESOL): -0.67
Log S (SILICOS-IT): 0.36
LogP: 1.09
MLOGP: -1.4
PSA

安全信息

安全说明

危险性质：非危险化学品

生产及用途

用途与制备

作为医药中间体，用于相关药物研发与合成（具体应用场景参考相关专利及文献）。

医药

合成路线 1（1. 合成：13490-32-9）

产率：93.5% 合成条件：Stage #1: With hydrogenchloride; sodium nitrite In water at 10℃; for 0.50 h; Cooling with ice Stage #2: With hydroxylamine hydrochloride; potassium hydroxide In water at 0℃; for 12.50 h; Reflux 实验步骤：将原料丙二腈（50.0g，0.76mol，1.0当量）加入到四颈瓶中并通过加热（约50℃）溶解。加入水（0.5L），在约10℃的冰水浴中加入，并加入分批加入亚硝酸钠（57.72g，0.83mol，1.1当量）。加入后，在10℃或更低的温度下滴加盐酸（6N，8.5mL）。将混合物在冰水浴中搅拌0.5小时。温度恒定，将上述反应溶液命名为A.H2NOH·HCl（158.4g，2.28mol，3.0当量）溶于水（255mL）中。氢氧化钾溶液（127.9g，2.28mol，3.0）向其中加入eq）水（255mL），加入混合物。将混合物在室温（25℃）下搅拌10分钟，将上述反应溶液指定为B.A的反应液为用冰水浴冷却至0℃-10℃，将B反应液滴加到A反应液中，滴加混合物，搅拌0.5小时。冰水浴，温度保持恒定，除去冰水浴，将混合物加热回流12小时。反应完成后，在冰水浴中滴加盐酸（6N，120mL）。（0℃）调节pH = 7.继续搅拌40分钟，抽滤反应溶液，用水洗涤滤饼，排出滤饼。目标化合物（101g，产率：获得93.5％）。 参考文献：

[1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10532 - 10535 [2] Patent: CN108727361, 2018, A. Location in patent: Paragraph 0150; 0152-0154 [3] Patent: TW2018/23219, 2018, A. Location in patent: Page/Page column 31; 32 [4] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 4, p. 156 - 162 [5] Patent: WO2016/40458, 2016, A2. Location in patent: Page/Page column 25; 26 [6] Patent: WO2014/66834, 2014, A1. Location in patent: Paragraph 00184 [7] Patent: US2015/133674, 2015, A1. Location in patent: Paragraph 0270; 0271; 0272 [8] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 486 - 491 [9] Patent: CN108003112, 2018, A. Location in patent: Paragraph 0029; 0036; 0041; 0042; 0043 [10] Patent: WO2017/2078, 2017, A1. Location in patent: Page/Page column 19; 20 [11] ChemMedChem, 2018, vol. 13, # 1, p. 30 - 36 [12] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 4, p. 312 - 317 [13] Chemistry - A European Journal, 2016, vol. 22, # 35, p. 12527 - 12532 [14] Patent: CN106967004, 2017, A. Location in patent: Paragraph 0018; 0045; 0046 [15] Patent: CN108101899, 2018, A. Location in patent: Paragraph 0007; 0017; 0035; 0038; 0039; 0040 [16] Patent: CN106883224, 2017, A. Location in patent: Paragraph 0055; 0056; 0057 [17] Patent: CN106866648, 2017, A. Location in patent: Paragraph 0060-0062 [18] Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 253 - 255 [19] Chemistry - A European Journal, 2009, vol. 15, # 11, p. 2625 - 2634 [20] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7364 - 7367 [21] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 2, p. 381 - 385 [22] RSC Advances, 2015, vol. 5, # 27, p. 21422 - 21429 [23] Patent: CN105418534, 2016, A. Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0338 [24] Dalton Transactions, 2016, vol. 45, # 39, p. 15382 - 15389 [25] ChemPlusChem, 2017, vol. 82, # 11, p. 1315 - 1319 [26] Polyhedron, 2018, vol. 139, p. 148 - 154 [27] ChemPlusChem, 2018, vol. 83, # 5, p. 439 - 447 [28] CrystEngComm, 2018, vol. 20, # 30, p. 4321 - 4328 [29] Crystal Growth and Design, 2018, [30] Patent: WO2018/156443, 2018, A1. Location in patent: Page/Page column 28 [31] Dalton Transactions, 2018, vol. 47, # 36, p. 12661 - 12666 [32] Patent: CN108689958, 2018, A. Location in patent: Paragraph 0087-0089