Benzenemethanamine, N,N'-1,2-ethanediylidenebis[α-methyl-, [N(E),N'(E),αR,α'R]-rel- | 90580-93-1

• 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: Benzenemethanamine, N,N'-1,2-ethanediylidenebis[α-methyl-, [N(E),N'(E),αR,α'R]-rel-
• 英文别名: N,N'-bis<(R)-1-phenylethyl>-1,2-ethanediimine
• CAS: 90580-93-1
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: NHVLGFIUCGHDAF-XYGGEOSRSA-N

物化性质

• 沸点：
  379.3±45.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Benzenemethanamine, N,N'-1,2-ethanediylidenebis[α-methyl-, [N(E),N'(E),αR,α'R]-rel- 、 phenylmagnesium chloride 以47%的产率得到
  参考文献：
  名称：

  Bambridge Kimberley, Begley Michael J., Simpkins Nigel S., Tetrahedron Lett, 35 (1994) N 20, S 3391-3394

  摘要：

  DOI：
• 作为产物：
  描述：

  草酸醛 、 R(+)-alpha-甲基苄胺 在 甲酸 、 sodium sulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以80%的产率得到Benzenemethanamine, N,N'-1,2-ethanediylidenebis[α-methyl-, [N(E),N'(E),αR,α'R]-rel-
  参考文献：
  名称：

  Dieck, Heindirk tom; Dietrich, Joerg, Chemische Berichte, 1984, vol. 117, # 2, p. 694 - 701

  摘要：

  DOI：

文献信息

• Enantioselective Reduction of Ketones by Polymethylhydrosiloxane in the Presence of Chiral Zinc Catalysts
  作者：Hubert Mimoun、Jean Yves de Saint Laumer、Luca Giannini、Rosario Scopelliti、Carlo Floriani

  DOI：10.1021/ja990522i

  日期：1999.7.1

  Enantioselective reduction of ketones, particularly acetophenones, by polymethylhydrosiloxane (PMHS) to the corresponding secondary alcohols can be achieved with high yields and enantiomeric excesses (ee's) up to 88% in the presence of chiral zinc catalysts (eq 1). Two catalytic systems have been developed giving similar ee's: (i) System A: ZnEt2 + chiral diimine or diamine 1-10, (ii) System B: Zn(carboxylate)(2) + chiral diamine activated by Vitride. System B is inexpensive, stable, and ready to use in toluene, providing either (R) or (S) chiral secondary alcohols with 70-80% ee in the presence of (S,S)- or (R,R)-N,N'-ethylenebis-(1-phenylethylamine) (ebpe, 6). The reduction has been carried out at the 1 kg scale without scale-up problems. The ligand is cheap and is recovered at the end of reaction by simple distillation from residues of the organic phase. Both precursors ZnMe2.(S,S)-ebpe (A) and Zn(dea)2 (S,S)-ebpe(B) for systems A and B, respectively, have been isolated and characterized by X-ray structure and exhibit the same catalytic properties and the same ee's for the reduction of acetophenone as the in situ prepared catalytic system. The complex ZnEt2 (S,S)-ebpe) (A') reacts with benzaldehyde to give the seven-membered ring dimer complex La in which benzaldehyde inserts into the Zn-N bond of complex A'. Acetophenone also reacts with A' to give a similar seven-membered ring dimer complex Lb. Both La and Lb are catalysts for the enantioselective reduction of acetophenone by PMHS and gave activities and ee's similar to those of A'. Synthetic and mechanistic aspects of this new economical method are discussed in this paper.
• Maanen, Hendrik L. van; Kleijn, Henk; Jastrzebski, Johann T. B. H., Recueil des Travaux Chimiques des Pays-Bas, 1994, vol. 113, # 12, p. 567 - 572
  作者：Maanen, Hendrik L. van、Kleijn, Henk、Jastrzebski, Johann T. B. H.、Koten, Gerard van

  DOI：——

  日期：——
• The stereoselective synthesis of functionalized vicinal diamine systems by the double allylation reactions of “protected” 1,2-bis-imine precursors.
  作者：William L. Neumann、Milorad M. Rogic、T.Jeffrey Dunn

  DOI：10.1016/s0040-4039(00)79412-3

  日期：1991.10

  A diastereoselective synthesis of vicinal diamines via the reactions of allylic Grignard reagents with readily available "protected" 1,2-bisimines has been developed. This method has been extended to preparing optically pure diamines by the use of chiral 1,2-bisimine precursors.
• Simple synthesis of a C2 symmetric vicinal diamine: Highly diastereoselective Grignard addition to a chiral bis-imine
  作者：Kimberley Bambridge、Michael J. Begley、Nigel S. Simpkins

  DOI：10.1016/s0040-4039(00)76916-4

  日期：1994.5

  The reaction of the enantiomerically pure bis-imine derived from glyoxal and (R)-alpha-methylbenzylamine with PhMgCl in diethylether is highly diastereoselective, resulting in the selective formation of the C-2 symmetric vicinal diamine 7.
• VAN, DER STEEN FRED H.;KLEIJN, HENK;SPEK, ANTHONY L.;VAN, KOTEN GERARD, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 503-504
  作者：VAN, DER STEEN FRED H.、KLEIJN, HENK、SPEK, ANTHONY L.、VAN, KOTEN GERARD

  DOI：——

  日期：——