(3S,4R)-methyl 4-(t-butoxycarbonylamino)-1-(2-chloroacetyl)-5-oxopyrrolidine-3-carboxylate | 1613255-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4R)-methyl 4-(t-butoxycarbonylamino)-1-(2-chloroacetyl)-5-oxopyrrolidine-3-carboxylate
• 英文别名: methyl (3S,4R)-1-(2-chloroacetyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopyrrolidine-3-carboxylate
• CAS: 1613255-83-6
• 化学式: C₁₃H₁₉ClN₂O₆
• 分子量: 334.757
• InChiKey: XMZYZFNEDDVUME-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R)-methyl 4-(t-butoxycarbonylamino)-1-(2-chloroacetyl)-5-oxopyrrolidine-3-carboxylate 、 胸腺嘧啶 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以42%的产率得到(3S,4R)-methyl 4-(t-butoxycarbonylamino)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases

  摘要：

  Novel analogues of nucleosides tethered on a chiral pyrrolidin-2-one were prepared, but the imide functionality was unstable under basic conditions. Thus, the carbonyl group was removed from pyrrolidin-2-one, and nucleoside analogues bearing a pyrrolidine ring were synthesized, which were unaffected under basic conditions. A nucleoside dimer was also obtained, bearing a carbamate linkage between two units.Graphics for use in the Table of Contents.

  DOI：

  10.1007/s00706-014-1251-4
• 作为产物：
  描述：

  、 氯乙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以69%的产率得到(3S,4R)-methyl 4-(t-butoxycarbonylamino)-1-(2-chloroacetyl)-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases

  摘要：

  Novel analogues of nucleosides tethered on a chiral pyrrolidin-2-one were prepared, but the imide functionality was unstable under basic conditions. Thus, the carbonyl group was removed from pyrrolidin-2-one, and nucleoside analogues bearing a pyrrolidine ring were synthesized, which were unaffected under basic conditions. A nucleoside dimer was also obtained, bearing a carbamate linkage between two units.Graphics for use in the Table of Contents.

  DOI：

  10.1007/s00706-014-1251-4