[4-(2-oxo-2-piperidin-1-ylethylsulfanyl)phenyl]carbamic acid tert-butyl ester | 889099-04-1

• 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: [4-(2-oxo-2-piperidin-1-ylethylsulfanyl)phenyl]carbamic acid tert-butyl ester
• CAS: 889099-04-1
• 化学式: C₁₈H₂₆N₂O₃S
• 分子量: 350.482
• InChiKey: ORCFLAFEHLRJKX-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  470.6±30.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [4-(2-oxo-2-piperidin-1-ylethylsulfanyl)phenyl]carbamic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 {4-[2-(2-hydroxyethylamino)ethanesulfonyl]phenyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Searching for Cyclin-Dependent Kinase Inhibitors Using a New Variant of the Cope Elimination

  摘要：

  beta-Piperidinoethylsulfides are oxidized by m-chloroperbenzoic acid to intermediates containing both N-oxide and sulfone functions. These undergo a Cope-type elimination to a vinylsulfone that can be captured by amines to afford beta-aminoethylsulfones. When a beta-aminoethylsulfone group is linked to the 4-position of a phenyl group attached at N-2 of O6-cyclohexylmethylguanine, the resulting derivatives are inhibitors of the cyclin-dependent kinase CDK2. One of the most potent inhibitors (IC50 = 45 nM) contained a N-3-hydroxypropyl group on the aminoethylsulfonyl substituent. The crystal structure of this inhibitor bound to CDK2/cyclin A was determined and shows an unusual network of hydrogen bonds. The synthetic methodology developed can be utilized in multiple-parallel format and has numerous potential applications in medicinal chemistry.

  DOI：

  10.1021/ja060595j
• 作为产物：
  描述：

  2-(4-氨基苯基硫基)乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 [4-(2-oxo-2-piperidin-1-ylethylsulfanyl)phenyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Searching for Cyclin-Dependent Kinase Inhibitors Using a New Variant of the Cope Elimination

  摘要：

  beta-Piperidinoethylsulfides are oxidized by m-chloroperbenzoic acid to intermediates containing both N-oxide and sulfone functions. These undergo a Cope-type elimination to a vinylsulfone that can be captured by amines to afford beta-aminoethylsulfones. When a beta-aminoethylsulfone group is linked to the 4-position of a phenyl group attached at N-2 of O6-cyclohexylmethylguanine, the resulting derivatives are inhibitors of the cyclin-dependent kinase CDK2. One of the most potent inhibitors (IC50 = 45 nM) contained a N-3-hydroxypropyl group on the aminoethylsulfonyl substituent. The crystal structure of this inhibitor bound to CDK2/cyclin A was determined and shows an unusual network of hydrogen bonds. The synthetic methodology developed can be utilized in multiple-parallel format and has numerous potential applications in medicinal chemistry.

  DOI：

  10.1021/ja060595j