2-甲基-4-甲氧基苯胺 | 98820-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 2-甲基-4-甲氧基苯胺
• 英文名称: diethyl (R)-(1-aminoethyl)phosphonate hydrochloride
• 英文别名: (1R)-1-diethoxyphosphorylethanamine;hydrochloride
• CAS: 98820-85-0
• 化学式: C₆H₁₆NO₃P*ClH
• 分子量: 217.633
• InChiKey: YPNAFBJJHSWFNN-FYZOBXCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 2-甲基-4-甲氧基苯胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以78%的产率得到diethylphosphonate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid

  摘要：

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.

  DOI：

  10.1021/jm00151a005
• 作为产物：
  描述：

  diethyl ((R)-1-{[(S)-tert-butanesulfinyl]amino}ethyl)phosphonate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到2-甲基-4-甲氧基苯胺
  参考文献：
  名称：

  亚磷酸二烷基酯与叔丁烷亚磺酰基亚胺的不对称合成α-氨基膦酸酯

  摘要：

  摘要 的KHMDS介导的另外的二烷基磷酸酯到ñ -叔-butanesulfinyl醛亚胺和均匀的高的产率和非对映选择性酮亚胺前进，从而使α-氨基膦酸酯的迅速和一般不对称合成。 的KHMDS介导的另外的二烷基磷酸酯到ñ -叔-butanesulfinyl醛亚胺和均匀的高的产率和非对映选择性酮亚胺前进，从而使α-氨基膦酸酯的迅速和一般不对称合成。

  DOI：

  10.1055/s-0033-1339712

文献信息

• Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
  作者：Frank R. Atherton、Cedric H. Hassall、Robert W. Lambert

  DOI：10.1021/jm00151a005

  日期：1986.1

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.
• Asymmetric Synthesis of α-Aminophosphonate Esters by the Addition of Dialkyl Phosphites to tert-Butanesulfinyl Imines
  作者：Jonathan Ellman、Hasan Khan

  DOI：10.1055/s-0033-1339712

  日期：——

  Abstract The KHMDS-mediated addition of dialkyl phosphites to N-tert-butanesulfinyl aldimines and ketimines proceeds in uniformly high yields and diastereoselectivities and thereby enables the rapid and general asymmetric synthesis of α-aminophosphonate esters. The KHMDS-mediated addition of dialkyl phosphites to N-tert-butanesulfinyl aldimines and ketimines proceeds in uniformly high yields and d

  摘要 的KHMDS介导的另外的二烷基磷酸酯到ñ -叔-butanesulfinyl醛亚胺和均匀的高的产率和非对映选择性酮亚胺前进，从而使α-氨基膦酸酯的迅速和一般不对称合成。 的KHMDS介导的另外的二烷基磷酸酯到ñ -叔-butanesulfinyl醛亚胺和均匀的高的产率和非对映选择性酮亚胺前进，从而使α-氨基膦酸酯的迅速和一般不对称合成。