(3S,4R,1'S)-4-methoxycarbonyl-1-[1'-(4-methoxyphenyleth-1'-yl)]-4-methyl-3-trichloroacetylaminopyrrolidin-2-one | 1206626-05-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R,1'S)-4-methoxycarbonyl-1-[1'-(4-methoxyphenyleth-1'-yl)]-4-methyl-3-trichloroacetylaminopyrrolidin-2-one
• 英文别名: methyl (3R,4S)-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methyl-5-oxo-4-[(2,2,2-trichloroacetyl)amino]pyrrolidine-3-carboxylate
• CAS: 1206626-05-2
• 化学式: C₁₈H₂₁Cl₃N₂O₅
• 分子量: 451.734
• InChiKey: REJXWVXGUXLEBZ-MNRXQERYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,1'S)-4-methoxycarbonyl-1-[1'-(4-methoxyphenyleth-1'-yl)]-4-methyl-3-trichloroacetylaminopyrrolidin-2-one 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以83%的产率得到(3S,4R)-4-methoxycarbonyl-4-methyl-3-trichloroacetylaminopyrrolidin-2-one
  参考文献：
  名称：

  A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

  摘要：

  Conformationally restricted analogues of beta-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at CA, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.004
• 作为产物：
  描述：

  (3S,4R,1'S)-4-methoxycarbonyl-3-trichloroacetylamino-1-[1'-(4''-methoxyphenyl)ethyl]pyrrolidin-2-one 、 碘甲烷 在 lithium hexamethyldisilazane 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (3S,4R,1'S)-4-methoxycarbonyl-1-[1'-(4-methoxyphenyleth-1'-yl)]-4-methyl-3-trichloroacetylaminopyrrolidin-2-one 、 (3S,4S,1'S)-4-methoxycarbonyl-1-[1'-(4-methoxyphenyleth-1'-yl)]-4-methyl-3-trichloroacetylaminopyrrolidin-2-one
  参考文献：
  名称：

  A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

  摘要：

  Conformationally restricted analogues of beta-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at CA, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.004

文献信息

• A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones
  作者：Emanuela Crucianelli、Roberta Galeazzi、Gianluca Martelli、Mario Orena、Samuele Rinaldi、Piera Sabatino

  DOI：10.1016/j.tet.2009.10.004

  日期：2010.1

  Conformationally restricted analogues of beta-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at CA, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring. (C) 2009 Elsevier Ltd. All rights reserved.