N,N-diphenyl-(2R,4R)-pentanediamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diphenyl-(2R,4R)-pentanediamine
• 英文别名: (2R,4R)-2-N,4-N-diphenylpentane-2,4-diamine
• 化学式: C₁₇H₂₂N₂
• 分子量: 254.375
• InChiKey: SSCVVXSPHURNGK-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S,4S)-(+)-戊二醇 在 2,6-二甲基吡啶 、 N,N,N',N'-四甲基胍叠氮化物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.25h， 生成 N,N-diphenyl-(2R,4R)-pentanediamine
  参考文献：
  名称：

  Enantioselective Synthesis of ansa-Zirconocenes

  摘要：

  The reaction of the chiral chelated bis-amide complex Zr{(2R,4R)-PhNCHMeCH2CHMeNPh}Cl2(THF)2 (R,R-7) with lithium ansa-bis-indenyl reagents Li2[SBI](Et2O) (8a, SBI = (1-indenyl)2SiMe2) or Li2[EBI](Et2O) (8b, EBI = 1,2-(1-indenyl)2ethane) in THF affords the corresponding ansa-zirconocenes S,S-(SBI)Zr{(2R,4R)-PhNCHMeCH2CHMeNPh} (S,S,R,R-9a) or S,S-(EBI)Zr{(2R,4R)-PhNCHMeCH2CHMeNPh} (S,S,R,R-9b) in >95% isolated yield and >99% enantiomeric excess. Compound 9b was converted to the corresponding enantiomerically pure dichloride S,S-(EBI)ZrCl2 (S,S-10b) in 91% isolated yield by reaction with HCl in Et2O. The chiral diamine (2R,4R)-HPhNCHMeCH2CHMeNHPh (R,R-5) was recovered from this reaction.

  DOI：

  10.1021/ja045245g

文献信息

• Enantioselective Synthesis of <i>ansa</i>-Zirconocenes
  作者：Matthew D. LoCoco、Richard F. Jordan

  DOI：10.1021/ja045245g

  日期：2004.11.1

  The reaction of the chiral chelated bis-amide complex Zr(2R,4R)-PhNCHMeCH2CHMeNPh}Cl2(THF)2 (R,R-7) with lithium ansa-bis-indenyl reagents Li2[SBI](Et2O) (8a, SBI = (1-indenyl)2SiMe2) or Li2[EBI](Et2O) (8b, EBI = 1,2-(1-indenyl)2ethane) in THF affords the corresponding ansa-zirconocenes S,S-(SBI)Zr(2R,4R)-PhNCHMeCH2CHMeNPh} (S,S,R,R-9a) or S,S-(EBI)Zr(2R,4R)-PhNCHMeCH2CHMeNPh} (S,S,R,R-9b) in >95% isolated yield and >99% enantiomeric excess. Compound 9b was converted to the corresponding enantiomerically pure dichloride S,S-(EBI)ZrCl2 (S,S-10b) in 91% isolated yield by reaction with HCl in Et2O. The chiral diamine (2R,4R)-HPhNCHMeCH2CHMeNHPh (R,R-5) was recovered from this reaction.
• Asymmetric Coordination Polymerization of Acrylamides by Enantiomeric Metallocenium Ester Enolate Catalysts
  作者：Garret M. Miyake、Wesley R. Mariott、Eugene Y.-X. Chen

  DOI：10.1021/ja072073p

  日期：2007.5.1

  Optically active, rigid one-handed helical poly(N,N-diaryl acrylamide)s and their copolymers with the randomly coiled methacrylate blocks were synthesized using the asymmetric coordination polymerization rendered by enantiomeric ansa-zirconocenium ester enolate catalysts under ambient conditions.