2-ethoxyethaneseleninic acid | 1233477-08-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硒酸及其衍生物
• 英文名称: 2-ethoxyethaneseleninic acid
• 英文别名: EtOCH2CH2SeO2H；2-Ethoxyethaneseleninic acid
• CAS: 1233477-08-1
• 化学式: C₄H₁₀O₃Se
• 分子量: 185.082
• InChiKey: WFISFTYWMLIVOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxyethaneseleninic acid 、 胞苷 在 七氟丁酸 作用下， 以 水 为溶剂， 反应 48.0h， 以38%的产率得到4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-ethoxyethylselanyl)pyrimidin-2-one
  参考文献：
  名称：

  Electrophilic Aromatic Selenylation: New OPRT Inhibitors

  摘要：

  2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.

  DOI：

  10.1021/ol1010032
• 作为产物：
  描述：

  bis(2-ethoxyethyl)diselenide 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.08h， 以96%的产率得到2-ethoxyethaneseleninic acid
  参考文献：
  名称：

  Electrophilic Aromatic Selenylation: New OPRT Inhibitors

  摘要：

  2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.

  DOI：

  10.1021/ol1010032

文献信息

• Mechanism of a Redox Coupling of Seleninic Acid with Thiol
  作者：Mohannad Abdo、Spencer Knapp

  DOI：10.1021/jo300156x

  日期：2012.4.6

  Equimolar quantities of 2-ethoxyethaneseleninic acid and p-thiocresol react rapidly in dichloromethane solution to give the selenosulfide along with disulfide, diselenide, and two products oxidized at sulfur, the thiosulfonate and the selenosulfonate. The latter two are new for this sort of coupling; their formation may be the result of an early thioseleninate to selenosulfinate isomerization. A radical chain mechanism is proposed to account for all five products, as well as their relative amounts.
• Electrophilic Aromatic Selenylation: New OPRT Inhibitors
  作者：Mohannad Abdo、Yong Zhang、Vern L. Schramm、Spencer Knapp

  DOI：10.1021/ol1010032

  日期：2010.7.2

  2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.