(S)-N,N-diphenyl-2-pyrrolidinemethanamine | 223769-30-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N,N-diphenyl-2-pyrrolidinemethanamine
• 英文别名: N-phenyl-N-[[(2S)-pyrrolidin-2-yl]methyl]aniline
• CAS: 223769-30-0
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: URHJQUBQJPFGEN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  三甲基乙酰氯 、 (S)-N,N-diphenyl-2-pyrrolidinemethanamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (S)-(-)-(2',2'-dimethylpropionyl)-2-<(N',N'-diphenylamino)methyl>pyrrolidine
  参考文献：
  名称：

  手性酰胺膦控制的有机铜锂试剂的不对称共轭加成反应

  摘要：

  对有机铜锂与查尔酮和环烯酮的不对称共轭加成反应中手性酰胺基膦1-14的行为的研究表明，反应效率受许多因素控制，包括铜盐，溶剂，铜与有机锂的分子比以及结构基板的。在化学计量条件下，与环烯酮的反应使加合物的收率高达94％ee。

  DOI：

  10.1016/s0040-4020(99)00094-0
• 作为产物：
  描述：

  (S)-1-(trifluoroacetyl)pyrrolidine-2-carboxylic acid 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-N,N-diphenyl-2-pyrrolidinemethanamine
  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.
• An asymmetric conjugate addition reaction of lithium organocopper reagent controlled by a chiral amidophosphine
  作者：Motomu Kanai、Yuichi Nakagawa、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(99)00094-0

  日期：1999.3

  Examination of the behaviors of the chiral amidophosphines 1–14 in the asymmetric conjugate addition reaction of lithium organocopper with chalcone and cycloalkenone revealed that the reaction efficiency is governed by many factors including copper salt, solvent, molecular ratio of copper and organolithium, and the structure of the substrate. The reaction with cycloalkenone gave the adduct in up to

  对有机铜锂与查尔酮和环烯酮的不对称共轭加成反应中手性酰胺基膦1-14的行为的研究表明，反应效率受许多因素控制，包括铜盐，溶剂，铜与有机锂的分子比以及结构基板的。在化学计量条件下，与环烯酮的反应使加合物的收率高达94％ee。