4-[1,3]dioxolan-2-yl-2-methyl-2-nitro-butyric acid ethyl ester | 109571-48-4

• 英文名称: 4-[1,3]dioxolan-2-yl-2-methyl-2-nitro-butyric acid ethyl ester
• 英文别名: 4-[1,3]Dioxolan-2-yl-2-methyl-2-nitro-buttersaeure-aethylester；Ethyl 4-(1,3-dioxolan-2-yl)-2-methyl-2-nitrobutanoate
• CAS: 109571-48-4
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: BIHRSRDYSDMSQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[1,3]dioxolan-2-yl-2-methyl-2-nitro-butyric acid ethyl ester 在 氯化铵 、 锌 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 27.0h， 以48%的产率得到5-(ethoxycarbonyl)-5-methyl-1-pyrroline N-oxide
  参考文献：
  名称：

  5-Carboxy-5-methyl-1-pyrroline N-oxide: a spin trap for the hydroxyl radical

  摘要：

  实时体内原位检测羟基自由基（HO˙）一直是生物学中自由基研究的一大挑战。虽然我们已经能够将这种自由基识别为HO˙的第二标志物，但发现5-羧基-5-甲基-1-吡咯啉N-氧化物2能够特异性地捕捉HO˙而牺牲超氧阴离子（O2˙−），为研究开辟了新的途径。特别是，硝酮2将使我们能够实时检测来自低剂量辐射的动物肿瘤中的HO˙。

  DOI：

  10.1039/b101945g
• 作为产物：
  描述：

  2-溴丙酸乙酯 在 间苯三酚 、 对甲苯磺酸 、 三乙胺 、 sodium nitrite 作用下， 以 二甲基亚砜 、 乙腈 、 苯 为溶剂， 反应 5.5h， 生成 4-[1,3]dioxolan-2-yl-2-methyl-2-nitro-butyric acid ethyl ester
  参考文献：
  名称：

  Esters of 5-Carboxyl-5-methyl-1-pyrroline N-Oxide:  A Family of Spin Traps for Superoxide

  摘要：

  Apparent rate constants, at acidic pH and neutral pH for the reaction of a family of ester-containing 5-carboxyl-5-methyl-1-pyrroline N-oxides with superoxide (O-2(.-)) were estimated, using ferricytochrome c as a competitive inhibitor. It was of interest to note that the rate constants were similar among the different nitrones and not that significantly different from that found for 5-(diethoxyphosphoryl)-5-dimethyl-1-pyrroline N-oxide. At acidic pH, the rate constant for spin trapping O-2(.-) was 3-fold greater than that at physiological pH. Subsequent experiments determined the half-life of aminoxyls, derived from the reaction of these nitrones with O-2(.-). The EPR spectra were modeled by using a global analysis method. The results clearly demonstrated that EPR spectra of all the aminoxyls were inconsistent with a model that included a single gamma-hydrogen splitting. A better interpretation modeled them as two diastereomers with identical nitrogen splittings and slightly different beta-hydrogen splittings. Detailed line width analyses slightly favored an equal line width-unequal population ratio for the two diastereomers.

  DOI：

  10.1021/jo0350413

文献信息

• Bonnett et al., Journal of the Chemical Society, 1959, p. 2087,2092
  作者：Bonnett et al.

  DOI：——

  日期：——