(S)-[(2-cyanophenoxy)methyl]-15-crown-5 | 1610459-24-9

• 英文名称: (S)-[(2-cyanophenoxy)methyl]-15-crown-5
• CAS: 1610459-24-9
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: USXZFCQPUNGIQG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  79.17
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-[(2-cyanophenoxy)methyl]-15-crown-5 、 (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Chiral (2-cyanophenoxy)methyl-15-crown-5 in diastereomeric discrimination of amino acid esters according to the data of electrospray ionization mass spectrometry

  摘要：

  The ability of [(2-cyanophenoxy)methyl]-15-crown-5 lariat ether enantiomers to diastereomeric discrimination with respect to hydrochlorides of 1-phenylethylamine and methyl esters of alanine, phenylalanine, and phenylglycine was studied by electrospray ionization mass spectrometry. The mentioned crown ether is available in non-racemic form owing to the procedure of preferential crystallization of enantiomers of its precursor. The quantitative estimation of the differences in the formation of diastereomeric complexes between the crown ether and the guests was performed by two independent methods: application of the guests with isotopic markers and using an additive of achiral amine-displacer. Both approaches indicate the existence of a moderate chiral discrimination: The (S)-enantiomer of the crown ether binds prevailingly the (S)-enantiomer of the guest, and vice versa.

  DOI：

  10.1134/s1070428015110202
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 (2S)-1-(2-cyanophenoxy)-2,3-propanediol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 74.33h， 以25%的产率得到(S)-[(2-cyanophenoxy)methyl]-15-crown-5
  参考文献：
  名称：

  Chiral lariat ethers based on spontaneously resolved 3-(2-cyanophenoxy)propane-1,2-diol

  摘要：

  DOI：

  10.1134/s1070428014040319