dimethyl (4R)-4-(aminomethyl)-1-(4-methoxycarbonylphenyl)-3-methylimidazolidine-2,2-dicarboxylate | 1060729-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: dimethyl (4R)-4-(aminomethyl)-1-(4-methoxycarbonylphenyl)-3-methylimidazolidine-2,2-dicarboxylate
• CAS: 1060729-67-0
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: YFUWAHOGTJYHLV-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl (4R)-4-(aminomethyl)-1-(4-methoxycarbonylphenyl)-3-methylimidazolidine-2,2-dicarboxylate 在 三甲基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 21.0h， 以66%的产率得到aplaminal
  参考文献：
  名称：

  Total Synthesis of (−)-Aplaminal

  摘要：

  The total synthesis and assignment of absolute configuration of (-)-aplaminal (1), a cytotoxic metabolite from a sea hare possessing a triazobicyclo[3.2.1]octane skeleton, has been achieved. The synthesis entailed condensation of a monoprotected diamine (3) with dimethyl 2-oxomalonate (4) to generate the imidazolidine core (2). Introduction of the third nitrogen via Mitsunobu activation and azide displacement, followed by reduction and lactam formation (AIMe(3)), furnished (-)-aplaminal (1). Overall, the synthesis entailed 9 steps and proceeded in 19% overall yield.

  DOI：

  10.1021/ol801794f
• 作为产物：
  描述：

  dimethyl (S)-4-(azidomethyl)-1-(4-(methoxycarbonyl)phenyl)-3-methylimidazolidine-2,2-dicarboxylate 在 palladium hydroxide on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以90%的产率得到dimethyl (4R)-4-(aminomethyl)-1-(4-methoxycarbonylphenyl)-3-methylimidazolidine-2,2-dicarboxylate
  参考文献：
  名称：

  Total Synthesis of (−)-Aplaminal

  摘要：

  The total synthesis and assignment of absolute configuration of (-)-aplaminal (1), a cytotoxic metabolite from a sea hare possessing a triazobicyclo[3.2.1]octane skeleton, has been achieved. The synthesis entailed condensation of a monoprotected diamine (3) with dimethyl 2-oxomalonate (4) to generate the imidazolidine core (2). Introduction of the third nitrogen via Mitsunobu activation and azide displacement, followed by reduction and lactam formation (AIMe(3)), furnished (-)-aplaminal (1). Overall, the synthesis entailed 9 steps and proceeded in 19% overall yield.

  DOI：

  10.1021/ol801794f

文献信息

• Total Synthesis of (−)-Aplaminal
  作者：Amos B. Smith、Zhuqing Liu

  DOI：10.1021/ol801794f

  日期：2008.10.2

  The total synthesis and assignment of absolute configuration of (-)-aplaminal (1), a cytotoxic metabolite from a sea hare possessing a triazobicyclo[3.2.1]octane skeleton, has been achieved. The synthesis entailed condensation of a monoprotected diamine (3) with dimethyl 2-oxomalonate (4) to generate the imidazolidine core (2). Introduction of the third nitrogen via Mitsunobu activation and azide displacement, followed by reduction and lactam formation (AIMe(3)), furnished (-)-aplaminal (1). Overall, the synthesis entailed 9 steps and proceeded in 19% overall yield.