N-(methanesulfonyloxy)-O-phenylisourea | 651306-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(methanesulfonyloxy)-O-phenylisourea
• 英文别名: [(E)-[amino(phenoxy)methylidene]amino] methanesulfonate
• CAS: 651306-32-0
• 化学式: C₈H₁₀N₂O₄S
• 分子量: 230.244
• InChiKey: RIKPURNWBUTUAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(methanesulfonyloxy)-O-phenylisourea 在 sodium hypochlorite 、 nitronium tetrafluoborate 、 四丁基氟化铵 、 lithium chloride 、 sodium chloride 作用下， 以 硝基甲烷 、 氘代乙腈 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 10.5h， 生成 对氟硝基苯
  参考文献：
  名称：

  Unprecedented Chemistry of an Aryloxychlorodiazirine:  Generation of a Dihalodiazirine and Diazirinone

  摘要：

  The reaction of p-nitrophenoxychlorodiazirine with tetrabutylammonium fluoride follows three channels: (1) approximately 17% of p-nitrophenoxide/fluoride exchange to chlorofluorodiazirine and p-nitrophenol, (2) approximately 28% of Cl/F exchange to p-nitrophenoxyfluorodiazirine, and (3) approximately 55% of ipso fluoride attack, affording p-nitrofluorobenzene and the previously unknown diazirinone (diazacyclopropenone).

  DOI：

  10.1021/ja050103n
• 作为产物：
  描述：

  氰酸苯酯 在 吡啶 、 羟胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(methanesulfonyloxy)-O-phenylisourea
  参考文献：
  名称：

  Unprecedented Chemistry of an Aryloxychlorodiazirine:  Generation of a Dihalodiazirine and Diazirinone

  摘要：

  The reaction of p-nitrophenoxychlorodiazirine with tetrabutylammonium fluoride follows three channels: (1) approximately 17% of p-nitrophenoxide/fluoride exchange to chlorofluorodiazirine and p-nitrophenol, (2) approximately 28% of Cl/F exchange to p-nitrophenoxyfluorodiazirine, and (3) approximately 55% of ipso fluoride attack, affording p-nitrofluorobenzene and the previously unknown diazirinone (diazacyclopropenone).

  DOI：

  10.1021/ja050103n

文献信息

• Chlorofluorocarbene:  First UV Observation of a Dihalocarbene in Solution
  作者：Robert A. Moss、Jingzhi Tian、Ronald R. Sauers、Christopher Skalit、Karsten Krogh-Jespersen

  DOI：10.1021/ol701804m

  日期：2007.9.1

  Chlorofluorocarbene (ClCF), generated by laser flash photolysis of chlorofluorodiazirine, absorbs at 368 nm in pentane. Absolute rate constants are reported for ClCF additions to several alkenes and pyridine. ClCF is less reactive toward alkenes than CCl(2), and it does not react rapidly with oxygen. Pertinent computational studies are included.

  氯氟重氮的激光闪光光解产生的氯氟卡宾（ClCF）在戊烷中的吸收波长为368 nm。报道了ClCF加到几种烯烃和吡啶中的绝对速率常数。ClCF对烯烃的反应性低于CCl（2），并且不会与氧气快速反应。包括相关的计算研究。
• Moss, Robert A.; Wang, Lei; Krogh-Jespersen, Karsten, Journal of the American Chemical Society, 2009, vol. 131, p. 2128 - 2130
  作者：Moss, Robert A.、Wang, Lei、Krogh-Jespersen, Karsten

  DOI：——

  日期：——
• Unprecedented Chemistry of an Aryloxychlorodiazirine:  Generation of a Dihalodiazirine and Diazirinone
  作者：Robert A. Moss、Gaosheng Chu、Ronald R. Sauers

  DOI：10.1021/ja050103n

  日期：2005.3.1

  The reaction of p-nitrophenoxychlorodiazirine with tetrabutylammonium fluoride follows three channels: (1) approximately 17% of p-nitrophenoxide/fluoride exchange to chlorofluorodiazirine and p-nitrophenol, (2) approximately 28% of Cl/F exchange to p-nitrophenoxyfluorodiazirine, and (3) approximately 55% of ipso fluoride attack, affording p-nitrofluorobenzene and the previously unknown diazirinone (diazacyclopropenone).