(2'S)-2'-(methoxymethyl)[1,1']bipyrrolidinyl-2,5-dione | 606143-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2'S)-2'-(methoxymethyl)[1,1']bipyrrolidinyl-2,5-dione
• 英文别名: 1-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]pyrrolidine-2,5-dione
• CAS: 606143-29-7
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: IVSIZLBMOJHXDK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'S)-2'-(methoxymethyl)[1,1']bipyrrolidinyl-2,5-dione 在 palladium on activated charcoal ammonium formate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 (2'S)-2'-(methoxymethyl)-5-(4-methylbenzyl)[1,1']bipyrrolidinyl-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines

  摘要：

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00589-5
• 作为产物：
  描述：

  丁二酸酐 、 (S)-1-amino-2-(methoxymethyl)pyrrolidine 在 sodium acetate 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(2'S)-2'-(methoxymethyl)[1,1']bipyrrolidinyl-2,5-dione
  参考文献：
  名称：

  Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines

  摘要：

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00589-5

文献信息

• Asymmetric synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines
  作者：Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/s0957-4166(03)00589-5

  日期：2003.9

  An efficient methodology for the enantioselective synthesis of 5-arylmethylpyrrolidin-2-ones and 2-arylmethylpyrrolidines has been devised. The key step is the stereoselective hydrogenation of the N-acylhydrazonium salts obtained from the corresponding arylmethylene hydrazides. These highly conjugated compounds are readily prepared by reacting a chiral succinimide with a variety of arylmethyl Grignard reagents. Removal of the chiral auxiliary and Subsequent reduction complete the synthesis of the title Compounds. (C) 2003 Elsevier Ltd. All rights reserved.