(1R,3S)-1-N-ethyl-1,2,2-trimethylcyclopentane-1,3-diamine | 1220123-35-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,3S)-1-N-ethyl-1,2,2-trimethylcyclopentane-1,3-diamine
• CAS: 1220123-35-2
• 化学式: C₁₀H₂₂N₂
• 分子量: 170.298
• InChiKey: WRYJQSCPIJXYAW-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.05
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)-1-N-ethyl-1,2,2-trimethylcyclopentane-1,3-diamine 、 水杨醛 在 silica gel 作用下， 以 乙醇 为溶剂， 以92%的产率得到(1R,3S)-N¹-ethyl-N³-salicylidene-1,2,2-trimethylcyclopentane-1,3-diamine
  参考文献：
  名称：

  Novel tridentate ligands derived from (+)-camphoric acid for enantioselective ethylation of aromatic aldehydes

  摘要：

  Novel tridentate ligands were prepared from (+)-camphoric acid, using simple synthetic sequences. The synthesized ligands were used in enantioselective ethylations of benzaldehydes, showing enantioselectivities up to 92%, at room temperature. Extending the reaction to other aromatic aldehydes, very good results (almost quantitative yields and ee up to 97%, for m-anisaldehyde) were obtained. Structural features such as no substitution in the salicylaldehyde moiety of the Schiff base and an ethyl group in the nitrogen at the Cl position of the cyclopentane ring seem to be essential for obtaining high enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.017
• 作为产物：
  描述：

  D-樟脑酸 在 盐酸 、 sodium azide 、 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 48.0h， 生成 (1R,3S)-1-N-ethyl-1,2,2-trimethylcyclopentane-1,3-diamine
  参考文献：
  名称：

  Novel tridentate ligands derived from (+)-camphoric acid for enantioselective ethylation of aromatic aldehydes

  摘要：

  Novel tridentate ligands were prepared from (+)-camphoric acid, using simple synthetic sequences. The synthesized ligands were used in enantioselective ethylations of benzaldehydes, showing enantioselectivities up to 92%, at room temperature. Extending the reaction to other aromatic aldehydes, very good results (almost quantitative yields and ee up to 97%, for m-anisaldehyde) were obtained. Structural features such as no substitution in the salicylaldehyde moiety of the Schiff base and an ethyl group in the nitrogen at the Cl position of the cyclopentane ring seem to be essential for obtaining high enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.017

文献信息

• Enantioselective ethylation of aldehydes with 1,3-N-donor ligands derived from (+)-camphoric acid
  作者：Dina Murtinho、M. Elisa Silva Serra、A.M.d’A. Rocha Gonsalves

  DOI：10.1016/j.tetasy.2009.12.012

  日期：2010.1

  Derivatives of (+)-camphoric acid were prepared by a short and simple synthetic sequence and proved to be excellent ligands for the enantioselective ethylation of benzaldellyde with diethylzinc, with ees of up to 96% being obtained The most efficient ligand was tested with several aromatic alclehydes and ees of up to 99% were observed Structural features of the ligands are determinant for achieving high enantioselectivities. (c) 2009 Elsevier Ltd All rights reserved