(1R,1'R)-N,N'-bis[(2-hydroxy-1-phenyl)ethyl]ethylenediamine | 344799-36-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,1'R)-N,N'-bis[(2-hydroxy-1-phenyl)ethyl]ethylenediamine
• 英文别名: (2R)-2-[2-[[(1R)-2-hydroxy-1-phenylethyl]amino]ethylamino]-2-phenylethanol
• CAS: 344799-36-6
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: VHWFDSRBEPKDAT-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-N,N'-bis[(2-hydroxy-1-phenyl)ethyl]ethylenediamine 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (1R,1'R)-1,4-bis-[(2'-hydroxy-1'-phenyl)ethyl]piperazine
  参考文献：
  名称：

  Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(−)-phenylglycinol

  摘要：

  The synthesis of four new 2,3-dialkylpiperazines in yields of 70-99%, using (R)-(-)-phenylglycinol as a chiral inductor is described. The synthesis involved reduction of the oxazino-oxazine type derivatives obtained by condensation of glyoxal and phenylglycinol to give hydroxyethylenediamine precursors which were further condensed with glyoxal. butanedione and 1-phenyl-1,2-propanedione and then reduced to provide the corresponding piperazines. The stereochemical outcome is determined by the configuration of the bisoxazolidine precursors, which is in turn dictated by steric effects exerted by the substituents on the five membered ring. The structures of five derivatives were established by X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00036-2
• 作为产物：
  描述：

  (3R,7R,4aR,8aR)-perhydro[1,4]oxazino[3,2-b]-1,4-oxazine 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以97%的产率得到(1R,1'R)-N,N'-bis[(2-hydroxy-1-phenyl)ethyl]ethylenediamine
  参考文献：
  名称：

  Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(−)-phenylglycinol

  摘要：

  The synthesis of four new 2,3-dialkylpiperazines in yields of 70-99%, using (R)-(-)-phenylglycinol as a chiral inductor is described. The synthesis involved reduction of the oxazino-oxazine type derivatives obtained by condensation of glyoxal and phenylglycinol to give hydroxyethylenediamine precursors which were further condensed with glyoxal. butanedione and 1-phenyl-1,2-propanedione and then reduced to provide the corresponding piperazines. The stereochemical outcome is determined by the configuration of the bisoxazolidine precursors, which is in turn dictated by steric effects exerted by the substituents on the five membered ring. The structures of five derivatives were established by X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00036-2

文献信息

• Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(−)-phenylglycinol
  作者：Vı́ctor Santes、Elizabeth Gómez、Verónica Zárate、Rosa Santillan、Norberto Farfán、Susana Rojas-Lima

  DOI：10.1016/s0957-4166(01)00036-2

  日期：2001.2

  The synthesis of four new 2,3-dialkylpiperazines in yields of 70-99%, using (R)-(-)-phenylglycinol as a chiral inductor is described. The synthesis involved reduction of the oxazino-oxazine type derivatives obtained by condensation of glyoxal and phenylglycinol to give hydroxyethylenediamine precursors which were further condensed with glyoxal. butanedione and 1-phenyl-1,2-propanedione and then reduced to provide the corresponding piperazines. The stereochemical outcome is determined by the configuration of the bisoxazolidine precursors, which is in turn dictated by steric effects exerted by the substituents on the five membered ring. The structures of five derivatives were established by X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.