benzyl α-amino(diethylphosphono)acetate | 52039-22-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl α-amino(diethylphosphono)acetate
• 英文别名: (+/-) benzyl 2-(diethoxyphosphoryl)glycinate；diethyl benzyloxycarbonylaminomethylphosphonate；Benzyl-α-amino-diethylphosphonoacetat；Benzyl amino(diethoxyphosphoryl)acetate；benzyl 2-amino-2-diethoxyphosphorylacetate
• CAS: 52039-22-2
• 化学式: C₁₃H₂₀NO₅P
• 分子量: 301.279
• InChiKey: SILAHJPKKUNWKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±40.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl α-amino(diethylphosphono)acetate 在 盐酸 、 lithium tetrafluoroborate 、 magnesium sulfate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 58.17h， 生成 benzyl 2-[(2S,5R,11S)-8-(acetyloxymethyl)-3-oxo-11-phenyl-9-oxa-1,4-diazatricyclo[6.3.0.02,5]undecan-4-yl]-2-diethoxyphosphorylacetate
  参考文献：
  名称：

  Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays

  摘要：

  A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.

  DOI：

  10.1021/jo00046a030
• 作为产物：
  描述：

  benzyl 2-(tert-butyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到benzyl α-amino(diethylphosphono)acetate
  参考文献：
  名称：

  Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays

  摘要：

  A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.

  DOI：

  10.1021/jo00046a030

文献信息

• Heterocyclic amides
  申请人：Zeneca Limited

  公开号：US05521179A1

  公开（公告）日：1996-05-28

  The present invention relates to certain novel heterocyclic amides which are 1-pyridylacetamide compounds of formula I, set out herein, which are inhibitors of human leukocyte elastase (HLE), also known as human neutrophil elastase (HNE), making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated. The invention also includes intermediates useful in the synthesis of these heterocyclic amides, processes for preparing the heterocyclic amides, pharmaceutical compositions containing such heterocyclic amides and methods for their use.

  本发明涉及某些新颖的杂环酰胺，它们是式I所示的1-吡啶乙酰胺化合物，这些化合物是人类白细胞弹性蛋白酶（HLE）的抑制剂，也被称为人类中性粒细胞弹性蛋白酶（HNE），使它们在需要这种抑制作用时非常有用，例如用作药理学、诊断和相关研究工具以及治疗哺乳动物中HLE相关疾病。该发明还包括在合成这些杂环酰胺过程中有用的中间体，制备这些杂环酰胺的方法，含有这些杂环酰胺的药物组合物以及它们的使用方法。
• Antimicrobial Compounds
  申请人：BIOMERIEUX

  公开号：US20170158720A1

  公开（公告）日：2017-06-08

  An antimicrobial compound, as well as the salts, derivatives and analogues thereof, said compound being represented by the general formula (I): wherein R 1 represents a peptide part P1 or a peptide part P2.

  一种抗微生物化合物，以及其盐、衍生物和类似物，所述化合物由通式（I）表示： 其中R1代表肽部分P1或肽部分P2。
• Preparation of Amino(diethoxyphosphoryl)acetic Esters. Catalytic Hydrogenation of Diazo Compounds to Amines
  作者：Chihiro Shiraki、Hiromitsu Saito、Keiichi Takahashi、Chikahiro Urakawa、Tadashi Hirata

  DOI：10.1055/s-1988-27591

  日期：——

  tert-Butyl amino(diethoxyphosphoryl)acetate (2a) is prepared on a multigram scale from tert-butyl diethoxyphosphorylacetate (1a) in a facile two-step synthesis. The method involves the formation of diazo derivative 4 and subsequent catalytic hydrogenation. Compound 2a is also synthesized by reduction of the oxime derivative 3. Direct amination of diethoxyphosphorylacetic esters with chloramine gives other types of esters 2b-e in addition to the tert-butyl ester 2a.

  tert-丁基氨基(二乙氧基磷酸)乙酸酯（2a）是通过二步简便合成法从tert-丁基二乙氧基磷酸乙酸酯（1a）制备的，规模达到多克。该方法涉及叠氮衍生物4的形成及随后的催化氢化。化合物2a还可以通过对肟衍生物3的还原合成。此外，通过与氯胺进行直接胺化反应，二乙氧基磷酸乙酸酯还可合成其他类型的酯2b-e，除了tert-丁基酯2a之外。
• (Diphenylphosphinyl)hydroxylamine: A new reagent for electrophilic -amination
  作者：Ernest W. Colvin、Gordon W. Kirby、Arthur C. Wilson

  DOI：10.1016/s0040-4039(00)87720-5

  日期：1982.1

  O-(Diphenylphosphinyl)hydroxylamine efficiently aminates a variety of stabilised carbanions and certain Grignard reagents.

  O-（二苯基膦基）羟胺可有效地胺化各种稳定化的碳负离子和某些格氏试剂。
• Heterocyclic amides having HLE inhibiting activity
  申请人：ZENECA LIMITED

  公开号：EP0509769A2

  公开（公告）日：1992-10-21

  The present invention relates to certain novel heterocyclic amides which are 1-pyridylacetamide compounds of formula I, set out herein, which are inhibitors of human leukocyte elastase (HLE), also known as human neutrophil elastase (HNE), making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated. The invention also includes intermediates useful in the synthesis of these heterocyclic amides, processes for preparing the heterocyclic amides, pharmaceutical compositions containing such heterocyclic amides and methods for their use.

  本发明涉及某些新型杂环酰胺，它们是式I的1-吡啶基乙酰胺化合物，载于本发明中，它们是人白细胞弹性蛋白酶（HLE），也称为人中性粒细胞弹性蛋白酶（HNE）的抑制剂，使得它们在任何需要这种抑制的情况下都有用，例如在药理学、诊断学和相关研究中用作研究工具，以及在治疗哺乳动物中涉及HLE的疾病时。本发明还包括用于合成这些杂环酰胺的中间体、制备杂环酰胺的工艺、含有这些杂环酰胺的药物组合物及其使用方法。