(3S,4R,1'S)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methyl-1-[1'-(4-methoxyphenyleth-1'-yl)]pyrrolidin-2-one | 1206626-08-5

• 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)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methyl-1-[1'-(4-methoxyphenyleth-1'-yl)]pyrrolidin-2-one
• 英文别名: methyl (3R,4S)-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopyrrolidine-3-carboxylate
• CAS: 1206626-08-5
• 化学式: C₂₁H₃₀N₂O₆
• 分子量: 406.479
• InChiKey: FJRYEKXVTJHRIE-CQURBHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,1'S)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methyl-1-[1'-(4-methoxyphenyleth-1'-yl)]pyrrolidin-2-one 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以82%的产率得到(3S,4R)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methylpyrrolidin-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：

  methyl (3R,4S)-{4-(tert-butoxycarbonylamino)-1-[(1S)-1-(4-methoxyphenyl)ethyl]-5-oxopyrrolidin-3-yl}carboxylate 、 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)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methyl-1-[1'-(4-methoxyphenyleth-1'-yl)]pyrrolidin-2-one 、 (3S,4S,1'S)-3-t-butoxycarbonylamino-4-methoxycarbonyl-4-methyl-1-[1'-(4-methoxyphenyleth-1'-yl)]pyrrolidin-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

• Quaternary Centres as a Tool for Modulating Foldamer Conformation
  作者：Roberta Galeazzi、Gianluca Martelli、Andrea Mazzanti、Mario Orena、Samuele Rinaldi

  DOI：10.1002/chem.201102103

  日期：2011.11.4

  Centre refold: (3R,4S,1′S)‐4‐Amino‐1‐(1′‐(4‐methoxyphenyl)ethyl)‐3‐methyl‐5‐oxopyrrolidine‐3‐carboxylic acid (AMMOPC) gives a foldamer with an 8‐helix conformation. When it was inserted in the 12‐helix foldamer of (3R,4S,1′S)‐4‐amino‐1‐(1′‐(4‐methoxyphenyl)ethyl)‐5‐oxo‐pyrrolidine‐3‐carboxylic acid (AMOPC), it locally induced formation of an 8‐helix conformation (see figure).

  中心折叠：（3 R，4 S，1 'S）‐4‐氨基‐1‐（1′‐（4‐甲氧基苯基）乙基）‐3‐甲基‐5‐氧吡咯烷‐3‐羧酸（AMMOPC）得到具有8螺旋构象的折叠剂。当将其插入（3 R，4 S，1 'S）-4-氨基-1-（1'-（4-甲氧基苯基）乙基）-5-氧代吡咯烷-3-羧酸的12螺旋折叠剂中时酸（AMOPC），它会局部诱导8螺旋构象的形成（见图）。
• 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.