1-<<(bicyclo<1.1.1>pentylmethyl)carbonyl>oxy>-2(1H)-pyridinethione | 136379-22-1

• 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
• 英文名称: 1-<<(bicyclo<1.1.1>pentylmethyl)carbonyl>oxy>-2(1H)-pyridinethione
• 英文别名: (2-sulfanylidenepyridin-1-yl) 2-(1-bicyclo[1.1.1]pentanyl)acetate
• CAS: 136379-22-1
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: FHPVRFBHHAMQAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-<<(bicyclo<1.1.1>pentylmethyl)carbonyl>oxy>-2(1H)-pyridinethione 在 苯硫酚 作用下， 反应 0.5h， 以50%的产率得到1-methylbicyclo<1.1.1>pentane
  参考文献：
  名称：

  Round-trip radical probes: ring cleavage of the bicyclo[1.1.1]pentylcarbinyl radical

  摘要：

  The novel concept of a round-trip probe for radical intermediates in reaction mechanisms is proposed and defined in this paper. A round-trip radical probe undergoes skeletal rearrangements such that the radical is returned to its site of origin. These probes should be especially useful for the study of enzyme mechanisms, since the special requirements of the active site may lead to ambiguous results using standard nonround-trip radical probes. The ring cleavages and rearrangements of the bicyclo[1.1.1]pentylcarbinyl radical are described as the prototypical round-trip radical probe. We have measured the rate constant for the ring opening of the bicyclo[1.1.1]pentylcarbinyl radical over the temperature range -42 to 60-degrees-C and have determined a temperature-dependent function for the ring opening of log (k3/s-1) = 12.78 (+/- 0.26) - 7.79 (+/- 0.35)/THETA and a rate constant for ring opening of 1.15 x 10(7) s-1 at 25-degrees-C.

  DOI：

  10.1021/jo00023a034
• 作为产物：
  描述：

  1-氧化-2-巯基吡啶 、 双环[1.1.1]戊烷-1-乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到1-<<(bicyclo<1.1.1>pentylmethyl)carbonyl>oxy>-2(1H)-pyridinethione
  参考文献：
  名称：

  Round-trip radical probes: ring cleavage of the bicyclo[1.1.1]pentylcarbinyl radical

  摘要：

  The novel concept of a round-trip probe for radical intermediates in reaction mechanisms is proposed and defined in this paper. A round-trip radical probe undergoes skeletal rearrangements such that the radical is returned to its site of origin. These probes should be especially useful for the study of enzyme mechanisms, since the special requirements of the active site may lead to ambiguous results using standard nonround-trip radical probes. The ring cleavages and rearrangements of the bicyclo[1.1.1]pentylcarbinyl radical are described as the prototypical round-trip radical probe. We have measured the rate constant for the ring opening of the bicyclo[1.1.1]pentylcarbinyl radical over the temperature range -42 to 60-degrees-C and have determined a temperature-dependent function for the ring opening of log (k3/s-1) = 12.78 (+/- 0.26) - 7.79 (+/- 0.35)/THETA and a rate constant for ring opening of 1.15 x 10(7) s-1 at 25-degrees-C.

  DOI：

  10.1021/jo00023a034