(S)-N-ethyl-N-phenyl-2-pyrrolidinemethaneamine | 174150-87-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-ethyl-N-phenyl-2-pyrrolidinemethaneamine
• 英文别名: (S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine；N-ethyl-N-[[(2S)-pyrrolidin-2-yl]methyl]aniline
• CAS: 174150-87-9
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: SGYFASVGCQDOFA-LBPRGKRZSA-N

物化性质

• 沸点：
  315.2±15.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 (S)-N-ethyl-N-phenyl-2-pyrrolidinemethaneamine 以 甲苯 为溶剂， 生成 ((S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine)ZnEt2
  参考文献：
  名称：

  Synthesis of polylactide using a zinc complex containing (S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine

  摘要：

  The reaction between ZnCl2 and (S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine (S-EPP) as a chiral ligand affords [ZnCl2(S-EPP)], whose structure has been determined by X-ray crystallography. [ZnEt2(S-EPP)] has demonstrated high activity toward the polymerization of rac-lactide with a maximum turnover frequency (TOF) of 121. Despite the intended stereocontrol by employing a chiral ligand, however, the observed heterotacticity was limited to under 0.6. The MWDs of the PLAs were found to be modulated by changing the solvent or controlling the concentration of the monomer in the solution. The glass transition temperature (T-g) was critically dependent on the MW within the narrow MWD regime, but the dependence became significantly shallow when the MWD was broadened. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.09.021
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 (S)-N-ethyl-N-phenyl-2-pyrrolidinemethaneamine
  参考文献：
  名称：

  Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

  摘要：

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.

  DOI：

  10.1021/jo981808t
• 作为试剂：
  描述：

  乙基3-羟基-2-萘甲酸酯 在 氧气 、 (S)-N-ethyl-N-phenyl-2-pyrrolidinemethaneamine 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-diethyl 2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate 、 2,2'-dihydroxy-[1,1']binaphthalenyl-3,3'-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

  摘要：

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.

  DOI：

  10.1021/jo981808t

文献信息

• Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes
  作者：Makoto Nakajima、Irie Miyoshi、Kumiko Kanayama、Shun-ichi Hashimoto、Masahiro Noji、Kenji Koga

  DOI：10.1021/jo981808t

  日期：1999.4.1

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.
• Synthesis of polylactide using a zinc complex containing (S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine
  作者：Jong Hwa Jeong、Young Hun An、Youn K. Kang、Quang Trung Nguyen、Hyosun Lee、Bruce M. Novak

  DOI：10.1016/j.poly.2007.09.021

  日期：2008.1

  The reaction between ZnCl2 and (S)-N-ethyl-N-phenyl-2-pyrrolidinemethanamine (S-EPP) as a chiral ligand affords [ZnCl2(S-EPP)], whose structure has been determined by X-ray crystallography. [ZnEt2(S-EPP)] has demonstrated high activity toward the polymerization of rac-lactide with a maximum turnover frequency (TOF) of 121. Despite the intended stereocontrol by employing a chiral ligand, however, the observed heterotacticity was limited to under 0.6. The MWDs of the PLAs were found to be modulated by changing the solvent or controlling the concentration of the monomer in the solution. The glass transition temperature (T-g) was critically dependent on the MW within the narrow MWD regime, but the dependence became significantly shallow when the MWD was broadened. (C) 2007 Elsevier Ltd. All rights reserved.