(β-chloro-α-aminoethyl)phosphonic acid | 70350-66-2

• 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
• 英文名称: (β-chloro-α-aminoethyl)phosphonic acid
• 英文别名: (±)-1-amino-2-chloroethylphosphonic acid；1-amino-2-chloroethanephosphonic acid；(1-amino-2-chloro-ethyl)-phosphonic acid；(1-amino-2-chloroethyl)phosphonic acid
• CAS: 70350-66-2
• 化学式: C₂H₇ClNO₃P
• mdl: MFCD19232527
• 分子量: 159.509
• InChiKey: JRPJBULCCYHWNX-UHFFFAOYSA-N

物化性质

• 熔点：
  202-208 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  368.2±52.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (β-chloro-α-aminoethyl)phosphonic acid 、 N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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：

  aziridine-2-phosphonic acid 在 盐酸 作用下， 反应 0.33h， 以77%的产率得到(β-chloro-α-aminoethyl)phosphonic acid
  参考文献：
  名称：

  Aziridine-2-phosphonic acid, the valuable synthon for synthesis of 1-amino-2-functionalized ethanephosphonic acids

  摘要：

  DOI：

  10.1016/s0040-4020(01)96741-9

文献信息

• Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
  作者：Renzhe Qian、Jeannie Horak、Friedrich Hammerschmidt

  DOI：10.1080/10426507.2017.1284844

  日期：2017.6.3

  1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

  图形摘要摘要将多种腈还原为醛亚胺的二异丁基铝盐，向其中加入亚磷酸二异丙酯。相应的 1-氨基膦酸酯被脱保护得到外消旋 1-氨基膦酸或与 Boc2O 反应生成 N-Boc 保护的 1-氨基膦酸酯。2-苄硫基-1-(叔丁氧基羰基氨基)丙基膦酸酯的对映异构体通过手性HPLC从外消旋体获得并转化为(R)-和(S)-高半胱氨酸、(R)-和(S)-的膦酸类似物2-氨基丁酸和(S)-甲硫氨酸，通过手性HPLC测定，所有ee>97%。
• Zygmunt,J.; Mastalerz,P., Polish Journal of Chemistry, 1978, vol. 52, p. 2271 - 2273
  作者：Zygmunt,J.、Mastalerz,P.

  DOI：——

  日期：——
• (.beta.-Chloro-.alpha.-aminoethyl)phosphonic acids as inhibitors of alanine racemase and D-alanine-D-alanine ligase
  作者：Vo Quang Yen、Denis Carniato、Liliane Vo Quang、Anne Marie Lacoste、Eugene Neuzil、Francois Le Goffic

  DOI：10.1021/jm00151a024

  日期：1986.1

  The (beta-chloro-, (beta, beta-dichloro-, and (beta, beta, beta-trichloro-alpha-aminoethyl)phosphonic acids have been synthesized and their inhibitory properties on the alanine racemases [EC 5.1.1.1] and the D-Ala:D-Ala ligases [EC 6.3.2.4] from Pseudomonas aeruginosa and Streptococcus faecalis have been evaluated. The monochloro and the dichloro derivatives of Ala-P exhibit a strong inhibition on the racemases of the two species tested but do not behave as suicide substrates. Only the D-Ala:D-Ala ligase of S. faecalis is inhibited by these compounds. The poor antibacterial activity observed with beta-chloro- and beta, beta-dichloro-Ala-P might be enhanced by the peptide-transport strategy.
• Zygmunt, Jan; Mastalerz, Przemyslaw, Polish Journal of Chemistry, 1981, vol. 55, # 2, p. 411 - 414
  作者：Zygmunt, Jan、Mastalerz, Przemyslaw

  DOI：——

  日期：——
• ZYGMUNT, J., TETRAHEDRON, 1985, 41, N 21, 4979-4982
  作者：ZYGMUNT, J.

  DOI：——

  日期：——