ethyl 2-nitrooxyisobutyrate | 858195-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: ethyl 2-nitrooxyisobutyrate
• 英文别名: α-nitryloxy-isobutyric acid ethyl ester；α-Nitryloxy-isobuttersaeure-aethylester；2-Nitryloxy-2-methyl-propionsaeure-aethylester；Ethyl 2-methyl-2-nitrooxypropanoate；ethyl 2-methyl-2-nitrooxypropanoate
• CAS: 858195-82-1
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: YLWAQMBJLFVDQV-UHFFFAOYSA-N

物化性质

• 沸点：
  89-91 °C(Press: 10 Torr)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitrooxyisobutyrate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以67%的产率得到2-甲基-2-(硝基氧基)丙酸
  参考文献：
  名称：

  NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates – synthesis and biological activities##For part 2 see [1]

  摘要：

  Organic nitrates release nitric oxide when incubated with thiosalicylic acid. S-Nitrooxyacylated esters and amides of thiosalicylic acid, together with the corresponding salicylates, were synthesized in order to perform a first in vitro evaluation of these new nitrate-thiol-hybrid prodrugs. These prodrugs might release NO in vivo after biotransformation without the use of endogenous reductives. None of these prodrugs released NO spontaneously when dissolved in buffer solution, but they did activate soluble guanylyl cyclase and induced vasodilatation of phenylephrine-pretreated male Wistar rat aorta in a potency range between that of isosorbiddinitrate and glycerole trinitrate. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00110-5
• 作为产物：
  描述：

  2-羟基异丁酸乙酯 在 硝酸 、 乙酸酐 、 尿素 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到ethyl 2-nitrooxyisobutyrate
  参考文献：
  名称：

  NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates – synthesis and biological activities##For part 2 see [1]

  摘要：

  Organic nitrates release nitric oxide when incubated with thiosalicylic acid. S-Nitrooxyacylated esters and amides of thiosalicylic acid, together with the corresponding salicylates, were synthesized in order to perform a first in vitro evaluation of these new nitrate-thiol-hybrid prodrugs. These prodrugs might release NO in vivo after biotransformation without the use of endogenous reductives. None of these prodrugs released NO spontaneously when dissolved in buffer solution, but they did activate soluble guanylyl cyclase and induced vasodilatation of phenylephrine-pretreated male Wistar rat aorta in a potency range between that of isosorbiddinitrate and glycerole trinitrate. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00110-5

文献信息

• Alkaline Nitration. I. The Nitration of Amines with Cyanohydrin Nitrates¹
  作者：William D. Emmons、Jeremiah P. Freeman

  DOI：10.1021/ja01621a059

  日期：1955.8
• Fichter; Steinbuch, Helvetica Chimica Acta, 1943, vol. 26, p. 697
  作者：Fichter、Steinbuch

  DOI：——

  日期：——
• NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates – synthesis and biological activities##For part 2 see [1]
  作者：Stefan Endres、Andreas Hacker、Eike Noack、Georg Kojda、Jochen Lehmann

  DOI：10.1016/s0223-5234(99)00110-5

  日期：1999.11

  Organic nitrates release nitric oxide when incubated with thiosalicylic acid. S-Nitrooxyacylated esters and amides of thiosalicylic acid, together with the corresponding salicylates, were synthesized in order to perform a first in vitro evaluation of these new nitrate-thiol-hybrid prodrugs. These prodrugs might release NO in vivo after biotransformation without the use of endogenous reductives. None of these prodrugs released NO spontaneously when dissolved in buffer solution, but they did activate soluble guanylyl cyclase and induced vasodilatation of phenylephrine-pretreated male Wistar rat aorta in a potency range between that of isosorbiddinitrate and glycerole trinitrate. (C) 1999 Editions scientifiques et medicales Elsevier SAS.