1-(2-chloroethyl)-3-(1H-decafluorocyclohexyl)urea | 74788-84-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1-(2-chloroethyl)-3-(1H-decafluorocyclohexyl)urea
• 英文别名: 1-(2-Chloroethyl)-3-(2,2,3,3,4,4,5,5,6,6-decafluorocyclohexyl)urea；1-(2-chloroethyl)-3-(2,2,3,3,4,4,5,5,6,6-decafluorocyclohexyl)urea
• CAS: 74788-84-4
• 化学式: C₉H₇ClF₁₀N₂O
• 分子量: 384.604
• InChiKey: OOVZVLAVGCTQBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2-chloroethyl)-3-(1H-decafluorocyclohexyl)urea 在 甲酸 、 phosphate buffer 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 0.92h， 生成 1-(1H-decafluorocyclohexyl)-3-nitrosoimidazolidin-2-one
  参考文献：
  名称：

  Fluorinated analogs of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea: an attempt to control metabolism

  摘要：

  In seeking to block and thereby determine the role of the rapid in vivo hydroxylation of the cyclohexyl moiety of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) in relation to antitumor activity and tissue distribution, the 3-(1H-decafluorocyclohexyl) analogue (FCCNU) was synthesized. FCCNU showed marked toxicity and little activity against the intracerebral L1210 leukemia in mice. At pH 7 in phosphate buffer at room temperature FCCNU rapidly decomposed to give 1-(1H-decafluorocyclohexyl)-3-nitrosoimidazolidin-2-one (3) and thence, by loss of HF, the 1-(nonafluorocyclohexenyl) derivative (4); CCNU did not follow this decomposition pathway to any significant extent. Both 3 and 4 were unstable in the buffer, but each was isolated crystalline and characterized. The formation of 3 and 4 account for the biological properties of FCCNU.

  DOI：

  10.1021/jm00185a015
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 1-H-decafluorocyclohexylamine 以 乙醚 为溶剂， 以2.14 g的产率得到1-(2-chloroethyl)-3-(1H-decafluorocyclohexyl)urea
  参考文献：
  名称：

  Fluorinated analogs of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea: an attempt to control metabolism

  摘要：

  In seeking to block and thereby determine the role of the rapid in vivo hydroxylation of the cyclohexyl moiety of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) in relation to antitumor activity and tissue distribution, the 3-(1H-decafluorocyclohexyl) analogue (FCCNU) was synthesized. FCCNU showed marked toxicity and little activity against the intracerebral L1210 leukemia in mice. At pH 7 in phosphate buffer at room temperature FCCNU rapidly decomposed to give 1-(1H-decafluorocyclohexyl)-3-nitrosoimidazolidin-2-one (3) and thence, by loss of HF, the 1-(nonafluorocyclohexenyl) derivative (4); CCNU did not follow this decomposition pathway to any significant extent. Both 3 and 4 were unstable in the buffer, but each was isolated crystalline and characterized. The formation of 3 and 4 account for the biological properties of FCCNU.

  DOI：

  10.1021/jm00185a015

文献信息

• Fluorinated analogs of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea: an attempt to control metabolism
  作者：Allan B. Foster、Michael Jarman、Paul L. Coe、John Sleigh、J. Colin Tatlow

  DOI：10.1021/jm00185a015

  日期：1980.11

  In seeking to block and thereby determine the role of the rapid in vivo hydroxylation of the cyclohexyl moiety of 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU) in relation to antitumor activity and tissue distribution, the 3-(1H-decafluorocyclohexyl) analogue (FCCNU) was synthesized. FCCNU showed marked toxicity and little activity against the intracerebral L1210 leukemia in mice. At pH 7 in phosphate buffer at room temperature FCCNU rapidly decomposed to give 1-(1H-decafluorocyclohexyl)-3-nitrosoimidazolidin-2-one (3) and thence, by loss of HF, the 1-(nonafluorocyclohexenyl) derivative (4); CCNU did not follow this decomposition pathway to any significant extent. Both 3 and 4 were unstable in the buffer, but each was isolated crystalline and characterized. The formation of 3 and 4 account for the biological properties of FCCNU.