(3S,4S,1'S)-4-allyl-4-methoxycarbonyl-1-(1'-phenyleth-1'-yl)-3-trichloroacetylaminopyrrolidin-2-one | 1206626-17-6

• 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,4S,1'S)-4-allyl-4-methoxycarbonyl-1-(1'-phenyleth-1'-yl)-3-trichloroacetylaminopyrrolidin-2-one
• 英文别名: methyl (3S,4S)-5-oxo-1-[(1S)-1-phenylethyl]-3-prop-2-enyl-4-[(2,2,2-trichloroacetyl)amino]pyrrolidine-3-carboxylate
• CAS: 1206626-17-6
• 化学式: C₁₉H₂₁Cl₃N₂O₄
• 分子量: 447.746
• InChiKey: BVFROCBGNBGZNA-WRSAYESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4R,1'S)-4-methoxycarbonyl-1-(1'-phenylethyl)-3-(trichloroacetylamino)pyrrolidin-2-one 、 3-溴丙烯 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-allyl-4-methoxycarbonyl-1-(1'-phenyleth-1'-yl)-3-trichloroacetylaminopyrrolidin-2-one 、 (3S,4S,1'S)-4-allyl-4-methoxycarbonyl-1-(1'-phenyleth-1'-yl)-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.