(1R,3S)-N,N'-bis[4-methoxyphenylidene]-1,3-diamino-1,2,2-trimethylcyclopentane | 116481-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,3S)-N,N'-bis[4-methoxyphenylidene]-1,3-diamino-1,2,2-trimethylcyclopentane
• 英文别名: cis(1R,3S)-1,3-di-(p-methoxybenzylideneamino)-1,2,2-trimethylcyclopentane；1-(4-methoxyphenyl)-N-[(1S,3R)-3-[(4-methoxyphenyl)methylideneamino]-2,2,3-trimethylcyclopentyl]methanimine
• CAS: 116481-00-6
• 化学式: C₂₄H₃₀N₂O₂
• 分子量: 378.514
• InChiKey: CMVFNBVLONICGF-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)-N,N'-bis[4-methoxyphenylidene]-1,3-diamino-1,2,2-trimethylcyclopentane 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 以99%的产率得到(1R,3S)-N,N'-bis(4-methoxybenzyl)-1,3-diamino-1,2,2-trimethylcyclopentane
  参考文献：
  名称：

  Enantioselective alkylation of aromatic aldehydes with (+)-camphoric acid derived chiral 1,3-diamine ligands

  摘要：

  A series of chiral 1,3-diamine ligands derived from (+)-camphoric acid were prepared from the reaction of 1,3-diamino-1,2,2-trimethylcyclopentane with aromatic aldehydes, followed by reduction of the corresponding diimines. These newly synthesized ligands were tested in the enantioselective alkylation of benzaldehyde with diethylzinc, giving 1-phenyl-l-propanol with enantiomeric ratios of up to 86:14. Our most selective ligand, derived from 2-methoxybenzaldehyde, was also tested in the alkylation,of several aromatic aldehydes and product alcohols with enantiomeric ratios of up to 93.5:6.5 being observed in 2 h at room temperature in the presence of 5 mol % ligand. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.01.013
• 作为产物：
  描述：

  D-樟脑酸 在 sodium azide 、 硫酸 、 对甲苯磺酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.25h， 生成 (1R,3S)-N,N'-bis[4-methoxyphenylidene]-1,3-diamino-1,2,2-trimethylcyclopentane
  参考文献：
  名称：

  Enantioselective alkylation of aromatic aldehydes with (+)-camphoric acid derived chiral 1,3-diamine ligands

  摘要：

  A series of chiral 1,3-diamine ligands derived from (+)-camphoric acid were prepared from the reaction of 1,3-diamino-1,2,2-trimethylcyclopentane with aromatic aldehydes, followed by reduction of the corresponding diimines. These newly synthesized ligands were tested in the enantioselective alkylation of benzaldehyde with diethylzinc, giving 1-phenyl-l-propanol with enantiomeric ratios of up to 86:14. Our most selective ligand, derived from 2-methoxybenzaldehyde, was also tested in the alkylation,of several aromatic aldehydes and product alcohols with enantiomeric ratios of up to 93.5:6.5 being observed in 2 h at room temperature in the presence of 5 mol % ligand. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.01.013

文献信息

• N,N?-Acylated 2,4-diazabicyclo[3.3.1]nonanes and 2,4-diazabicyclo [3.2.1]octanes from alicyglic bisazomethines
  作者：N. E. Agafonov、G. Ya. Kondrat'eva、V. S. Bogdanov

  DOI：10.1007/bf01455484

  日期：1988.4