(2R,5R)-1-benzyl-2,5-bis(chloromethyl)pyrrolidine

• 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: (2R,5R)-1-benzyl-2,5-bis(chloromethyl)pyrrolidine
• 化学式: C₁₃H₁₇Cl₂N
• 分子量: 258.191
• InChiKey: LMEDTOVDYJYXAF-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-benzyl-2,5-bis(chloromethyl)pyrrolidine 在 palladium dihydroxide 氢气 作用下， 生成 (2S,5S)-2,5-Diethylpyrrolidine
  参考文献：
  名称：

  Enantioselective palladium catalyzed allylic alkylation with C2-symmetric chiral diamine ligands

  摘要：

  A C-2-symmetric chiral diamine ligand 1 was found to be effective for palladium catalyzed asymmetric allylic substitution of racemic 1,3-diphenyl-2-propenyl acetate 5 with dimethyl malonate. The X-ray analysis and NMR study of the palladium complex 7 with chiral diamine 1 have revealed the mechanism of high enantioselection.

  DOI：

  10.1016/s0040-4039(00)61472-7
• 作为产物：
  描述：

  1-Benzyl-[(2R,5R)-2,5-bis(hydroxymethyl)]pyrrolidine 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 (2R,5R)-1-benzyl-2,5-bis(chloromethyl)pyrrolidine
  参考文献：
  名称：

  Design and synthesis of novel chiral pyrrolidine-based diamines with C2-symmetry

  摘要：

  Novel chiral pyrrolidine-based diamines with C2-symmetry 2, 3 and their related compounds 4 - 8 were designed and synthesized in optically pure forms. Both (+)- and (-)-2 were prepared from optical active ditosylate 9. 3 was prepared from 3,5-dimethylbenzaldehyde through optical resolution and its absolute stereochemistry was correlated with 2,3-dimethylsuccinate 27. 4 was prepared from (-)-diol 28. 5 - 8 were prepared from 9 and 11.

  DOI：

  10.1016/s0040-4020(01)80176-9

文献信息

• Design and synthesis of novel chiral pyrrolidine-based diamines with C2-symmetry
  作者：Makoto Nakajima、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4020(01)80176-9

  日期：1993.1

  Novel chiral pyrrolidine-based diamines with C2-symmetry 2, 3 and their related compounds 4 - 8 were designed and synthesized in optically pure forms. Both (+)- and (-)-2 were prepared from optical active ditosylate 9. 3 was prepared from 3,5-dimethylbenzaldehyde through optical resolution and its absolute stereochemistry was correlated with 2,3-dimethylsuccinate 27. 4 was prepared from (-)-diol 28. 5 - 8 were prepared from 9 and 11.
• Enantioselective palladium catalyzed allylic alkylation with C2-symmetric chiral diamine ligands
  作者：Hideki Kubota、Makoto Nakajima、Kenji Koga

  DOI：10.1016/s0040-4039(00)61472-7

  日期：1993.12

  A C-2-symmetric chiral diamine ligand 1 was found to be effective for palladium catalyzed asymmetric allylic substitution of racemic 1,3-diphenyl-2-propenyl acetate 5 with dimethyl malonate. The X-ray analysis and NMR study of the palladium complex 7 with chiral diamine 1 have revealed the mechanism of high enantioselection.