(S)-1-Benzyl-5-butyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-pyrrolidin-2-one | 506405-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-Benzyl-5-butyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-pyrrolidin-2-one
• 英文别名: (3S)-1-benzyl-5-butyl-3-[tert-butyl(dimethyl)silyl]oxy-5-hydroxypyrrolidin-2-one
• CAS: 506405-93-2
• 化学式: C₂₁H₃₅NO₃Si
• 分子量: 377.599
• InChiKey: GGKXGQVZBHNCRE-YMXDCFFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-Benzyl-5-butyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-pyrrolidin-2-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 (3S)-5-butyliden-3-(tert-butyldimethylsilyloxy)-1-benzyl-2-pyrrolidinone
  参考文献：
  名称：

  Regio- and diastereoselective synthesis of 5-trans-substituted and 5,5-disubstituted 2-pyrrolidinones derived from (S)-malic acid

  摘要：

  5-trans-Substituted 2-pyrrolidinones 6a, 6c and 6d and 5,5-disubstituted 2-pyrrolidinones 6e-k were regio- and diastereoselectively formed through the addition of organolithium species to imides 1a,b derived from malic acid, followed by addition of triethylsilane, allyltributyltin or TMSCN to the N-acyliminium ions formed in situ from the corresponding 5-hydroxy lactams. A short and diastereoselective synthesis of non-natural amino acid trans-4-hydroxy-D-proline is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00508-6
• 作为产物：
  描述：

  正丁基锂 、 (S)-1-benzyl-3-(tert-butyldimethylsilyloxy)pyrrolidine-2,5-dione 在 cerium(III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 (S)-1-Benzyl-5-butyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-pyrrolidin-2-one
  参考文献：
  名称：

  Regio- and diastereoselective synthesis of 5-trans-substituted and 5,5-disubstituted 2-pyrrolidinones derived from (S)-malic acid

  摘要：

  5-trans-Substituted 2-pyrrolidinones 6a, 6c and 6d and 5,5-disubstituted 2-pyrrolidinones 6e-k were regio- and diastereoselectively formed through the addition of organolithium species to imides 1a,b derived from malic acid, followed by addition of triethylsilane, allyltributyltin or TMSCN to the N-acyliminium ions formed in situ from the corresponding 5-hydroxy lactams. A short and diastereoselective synthesis of non-natural amino acid trans-4-hydroxy-D-proline is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00508-6

文献信息

• Regio- and diastereoselective synthesis of 5-trans-substituted and 5,5-disubstituted 2-pyrrolidinones derived from (S)-malic acid
  作者：Cristina M. Schuch、Ronaldo A. Pilli

  DOI：10.1016/s0957-4166(02)00508-6

  日期：2002.9

  5-trans-Substituted 2-pyrrolidinones 6a, 6c and 6d and 5,5-disubstituted 2-pyrrolidinones 6e-k were regio- and diastereoselectively formed through the addition of organolithium species to imides 1a,b derived from malic acid, followed by addition of triethylsilane, allyltributyltin or TMSCN to the N-acyliminium ions formed in situ from the corresponding 5-hydroxy lactams. A short and diastereoselective synthesis of non-natural amino acid trans-4-hydroxy-D-proline is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.