(S)-(1-Aminopropyl)phosphonsaeure-diethylester | 104549-64-6

• 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: (S)-(1-Aminopropyl)phosphonsaeure-diethylester
• 英文别名: diethyl (S)-(1-aminopropyl)phosphonate；(S)-diethyl 1-aminopropanephosphonate；(S)-diethyl 1-aminopropylphosphonate；(1S)-1-diethoxyphosphorylpropan-1-amine
• CAS: 104549-64-6
• 化学式: C₇H₁₈NO₃P
• 分子量: 195.199
• InChiKey: UWHFLDMTDWUUGG-ZETCQYMHSA-N

物化性质

• 沸点：
  258.9±23.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 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：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(1-Aminopropyl)phosphonsaeure-diethylester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 116.0h， 生成 N--O-methyl-(S)-tyrosine N-methyl amide
  参考文献：
  名称：

  Synthesis of novel N-phosphonoalkyl dipeptide inhibitors of human collagenase

  摘要：

  The synthesis of a series of N-phosphonoalkyl dipeptides 6 is described. Syntheses were devised that allowed the preparation of single diastereoisomers and the assignment of stereochemistry. The compounds were evaluated in vitro for their ability to inhibit the degradation of radiolabeled collagen by purified human lung fibroblast collagenase. Several of the compounds were potent collagenase inhibitors and were at least l0-fold more potent than their corresponding N-carboxyalkyl analogues. Activity was lost when the phosphonic acid group P(O)(OH)(2) was replaced by the phosphinic acid groups P(O)(H)(OH) and P(O)(Me)(OH). At the P-1 position, (R)- or (S)-allkyl groups, especially ethyl and methyl (e.g., 12a,b, 52a,b, and 53a,b), or an (R)-phenethyl moiety (55a) conferred high potency (IC50 values in the range 0.23-0.47 mu M). (S)-Stereochemistry was preferred for the P-1(') isobutyl side chain. Structure-activity relationships were also investigated at the P-2(') site, and interestingly, compounds with basic side chains such as the guanidine 57a, were equipotent with more lipophilic compounds, such as 52a. As with other series of collagenase inhibitors, potency was enhanced by introducing bicyclic aromatic P-2(') substituents. The most potent phosphonic acid of the series was the bicyclic aromatic P-2(') tryptophan analogue 59a (IC50 0.05 mu M).

  DOI：

  10.1021/jm00027a020
• 作为产物：
  描述：

  二乙基氨基甲烷膦酸酯 在 盐酸 、 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-(1-Aminopropyl)phosphonsaeure-diethylester
  参考文献：
  名称：

  手性膦酰甘氨酸当量的烷基化：α-氨基-α-烷基膦酸二乙酯的不对称合成

  摘要：

  建立了模型以合理化手性膦酰基甘氨酸等效物烷基化产生α-氨基-α-烷基膦酸酯的实验结果。使用半经验计算进行的模型研究强调了螯合作用在影响烷基化步骤的非对映选择性方面的作用。可以通过调节樟脑骨架碳C-1处取代基的官能度来优化螯合作用。如建模所建议，通过使用2d，化合物5（R = CH 3，C 2 H 5）的对映体过量得到了重大改善。

  DOI：

  10.1016/0040-4020(94)01059-9

文献信息

• Asymmetric Synthesis of Diethyl α-Amino-α-Alkyl-Phosphonates by Alkylation of the Chiral Schiff Base Derived from (+)-Ketopinic Acid and Diethylaminomethyl Phosphonate
  作者：M. Ferrari、G. Jommi、G. Miglierini、R. Pagliarin、M. Sisti

  DOI：10.1080/00397919208021082

  日期：1992.1

  chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-α-amino-α-alkyl phosphonates with high enantiomeric excesses when benzyl or allyl halides are used in the alkylation step. An improved procedure for the preparation of diethyl aminomethylphosphonate is also reported.

  摘要 当使用苄基或烯丙基卤化物时，由 (+)-酮品酸和氨基甲基膦酸二乙酯缩合得到的手性席夫碱烷基化，然后水解得到对映体过量的 (S)-α-氨基-α-烷基膦酸二乙酯。在烷基化步骤中。还报道了制备氨基甲基膦酸二乙酯的改进方法。
• Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates
  作者：Tadeusz Gajda

  DOI：10.1016/s0957-4166(00)86271-0

  日期：1994.10

  Reduction of diethyl alpha-ketophosphonates 1 with borane and B-butyloxazaborolidine 2 as catalyst afforded diethyl (S)- or (R)-1-hydroxyalkylphosphonates 3a-d or 3e-f respectively in good yields and moderate to good enantiomeric excess (53-83 ee%). Respective diethyl (R)- and (S)-1-aminoalkylphosphonates 6 were obtained in a one-pot transformation, by the Mitsunobu reaction of 1-hydroxyphosphonates 3 with hydrazoic acid, and subsequent treatment of the intermediate azides 4, with triphenylphosphine, followed by hydrolysis df the iminophosphoranes 5 with water.
• Enzymatic synthesis of optically active 1- and 2-aminoalkanephosphonates
  作者：Chengye Yuan、Chengfu Xu、Yonghui Zhang

  DOI：10.1016/s0040-4020(03)00995-5

  日期：2003.8

  A number of 1- and 2-aminoalkanephosphonates were resolved with high enantioselectivity by Candida antarctica lipase B-catalyzed acetylation. By this method, optically pure aminoalkanephosphonates and amidoalkanephosphonates, the precursors of the corresponding aminoalkanephosphonic acids, were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of diethyl α-amino- α-alkyl-phosphonates by alkylation of chiral phosphonoglycine equivalents: Role of chelating effects
  作者：Giancarlo Jommi、Giuliana Miglierini、Roberto Pagliarin、Guido Sello、Massimo Sisti

  DOI：10.1016/s0957-4166(00)82094-7

  日期：1992.9

  Diethyl alpha-amino-alpha-alkyl-phosphonates are obtained in good to high enantiomeric excesses by alkylation of chiral phosphonoglycine equivalents embodying the camphor skeleton. The chelating effects in the alkylation step play an important role in enhancing the diastereoselectivity of the reaction as substantiated by semiempirical calculations (AM1).
• SCHOLLKOPF U.; SCHUTZE R., LIEBIGS ANN. CHEM.,(1987) N 1, 45-49
  作者：SCHOLLKOPF U.、 SCHUTZE R.

  DOI：——

  日期：——