diethyl formylphosphonate | 119372-12-2

• 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: diethyl formylphosphonate
• 英文别名: formylphosphonic acid diethyl ester；Diethoxyphosphinylformaldehyde；diethoxyphosphorylformaldehyde
• CAS: 119372-12-2
• 化学式: C₅H₁₁O₄P
• 分子量: 166.114
• InChiKey: ROOOFIGWSLRHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl formylphosphonate 在 4-二甲氨基吡啶 、 三乙胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 240.0h， 生成 diethyl (3S,5S)-5-(acetoxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate
  参考文献：
  名称：

  Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines

  摘要：

  All the enantiomers of 0,0-diethyl 4-hydroxypyrrolidinyl-2-phosphonates, phosphonate analogues of cis- and trans-4hydroxyprolines, have been obtained for the first time. The synthetic strategy involved 1,3-dipolar cycloaddition of (R)- and (S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrones to ally] alcohol and separation of the corresponding 0,0-diethyl 5-(hydroxymethyl)-2-(1-phenylethyl)isoxazolidinyl-3-phosphonates, which were subsequently mesylated and hydrogenated to undergo intramolecular cyclisation. Absolute configurations of the enantiomeric proline phosphonates were established after N- and 0-derivatization with (S)-O-methylmandelic acid employing the Trost model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.006
• 作为产物：
  描述：

  羟甲基膦酸二乙酯 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.28h， 生成 diethyl formylphosphonate
  参考文献：
  名称：

  5取代异恶唑和异恶唑啉-3-膦酸酯的区域选择性途径。

  摘要：

  通过（二乙氧基磷酰基）甲腈氧化物与1-取代的炔烃和烯烃的1，3-偶极环加成反应，可选择性地合成5-取代的3-（二乙氧基磷酰基）异恶唑和-2-异恶唑啉。通过将此方法应用于N-（叔丁氧基羰基）-取代的烯丙基甘氨酸甲酯，我们制备了两个非对映体3-膦酰基-2-异恶唑啉-5-基取代的氨基酸的前体，它们是有效的NMDA受体拮抗剂的生物等排体。 。 环加成-区域选择性-膦酸酯-异恶唑-杂环

  DOI：

  10.1055/s-0028-1083343

文献信息

• Truncated phosphonated C-1′-branched N,O-nucleosides: A new class of antiviral agents
  作者：Roberto Romeo、Caterina Carnovale、Salvatore V. Giofrè、Giovanni Romeo、Beatrice Macchi、Caterina Frezza、Francesca Marino-Merlo、Venerando Pistarà、Ugo Chiacchio

  DOI：10.1016/j.bmc.2012.03.047

  日期：2012.6

  Truncated phosphonated C-1′-branched N,O-nucleosides have been synthesized in good yields by 1,3-dipolar cycloaddition methodology, starting from N-methyl-C-(diethoxyphosphoryl)nitrone 7. Preliminary biological assays show that β-anomers are able to inhibit HIV in vitro infection at concentrations in the micromolar range. Higher SI values with respect to AZT indicated that the compounds were endowed

  截短的膦酸化的C-1'-支链N，O-核苷都在良好的产率通过1,3-偶极环加成的方法被合成，从开始Ñ甲基Ç - （二乙氧基磷酰基）硝酮7。初步的生物学分析表明，β-端基异构体能够以微摩尔范围的浓度抑制HIV体外感染。相对于AZT，较高的SI值表明该化合物具有低细胞毒性。
• Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines
  作者：Dorota G. Piotrowska

  DOI：10.1016/j.tetasy.2008.01.009

  日期：2008.2

  Three enantiomerically pure diethyl 5-acetoxy-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonates were obtained by 1,3-dipolar cycloaddition of the title nitrone and vinyl acetate. Each of them was subsequently transformed into the respective 5-hydroxy derivatives, which exist as equilibrium mixtures of C5-anomers. Detailed mutarotation studies on a 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidine system

  通过标题腈和乙酸乙烯酯的1，3-偶极环加成反应得到三种对映体纯的5-乙酰氧基-2-[（（S）-1-苯基乙基）异恶唑啉基-3-膦酸二乙酯]。随后将它们各自转化成各自的5-羟基衍生物，它们以C5-端基异构体的平衡混合物形式存在。上的3-详细变旋研究（ø，ö -diethylphosphoryl）-5- hydroxyisoxazolidine系统显示，反式-异构体（3小号，5 - [R ）在固体状态下是有利的，而在后氯仿48小时d溶液它epimerises在C5为（3 S，5 S）-和（3 S，5 R）-异构体。主要的（3 S，5 S）异构体采用单个E 3构象，并通过C3-P（O）⋯HO-C5氢键稳定。基于使用1 H，13 C和31 P NMR数据进行的构象分析，确定了环加合物的绝对构型，并通过将（3 S，5 R）-异构体转化为已知的（S）-（+）-磷酸高丝氨酸来确认。
• SELECTIVE CASPASE INHIBITORS AND USES THEREOF
  申请人：Ahlfors Jan-Eric

  公开号：US20120157394A1

  公开（公告）日：2012-06-21

  The present invention relates to compounds of Formula I, II, IVC, VIIIC, IXC, or XC and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds for the selective inhibition of one or more caspases. Also described are methods where the compounds of Formula I, II, IVC, VIIIC, IXC, or XC are used in the prevention and/or treatment of various diseases and conditions in subjects, including caspase-mediated diseases such as sepsis, myocardial infarction, ischemic stroke, spinal cord injury (SCI), traumatic brain injury (TBI) and neurodegenerative disease (e.g. multiple sclerosis (MS) and Alzheimer's, Parkinson's, and Huntington's diseases). Processes for synthesizing tripeptides are provided.

  本发明涉及公式I、II、IVC、VIIIC、IXC或XC化合物及其药物用途。本发明的特定方面涉及使用这些化合物选择性地抑制一个或多个半胱氨酸蛋白酶的用途。还描述了使用公式I、II、IVC、VIIIC、IXC或XC化合物在受试者中预防和/或治疗各种疾病和病状的方法，包括半胱氨酸蛋白酶介导的疾病，如败血症、心肌梗塞、缺血性卒中、脊髓损伤（SCI）、创伤性脑损伤（TBI）和神经退行性疾病（例如多发性硬化症（MS）和阿尔茨海默病、帕金森病和亨廷顿病）。还提供了三肽合成的方法。
• Selective Caspase Inhibitors and Uses Thereof
  申请人：Ahlfors Jan-Eric

  公开号：US20110077190A1

  公开（公告）日：2011-03-31

  The present invention relates to compounds of Formula I, IA, II, HA, III, or IHA and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds for the selective inhibition of one or more caspases. Also described are methods where the compounds of Formula I, IA, II, IIA, III, or IIIA are used in the prevention and/or treatment of various diseases and conditions in subjects, including caspase-mediated diseases such as sepsis, myocardial infarction, ischemic stroke, spinal cord injury (SCI), traumatic brain injury (TBI) and neurodegenerative disease (e.g. multiple sclerosis (MS) and Alzheimer's, Parkinson's, and Huntington's diseases).

  本发明涉及公式I，IA，II，HA，III或IHA的化合物及其药物用途。本发明的特定方面涉及使用这些化合物选择性地抑制一个或多个半胱氨酸蛋白酶的用途。还描述了使用公式I，IA，II，IIA，III或IIIA的化合物防治受试者的各种疾病和病况的方法，包括半胱氨酸蛋白酶介导的疾病，如败血症、心肌梗死、缺血性中风、脊髓损伤（SCI）、创伤性脑损伤（TBI）和神经退行性疾病（例如多发性硬化症（MS）和阿尔茨海默病、帕金森病和亨廷顿病）。
• Selective caspase inhibitors and uses thereof
  申请人：Ahlfors Jan-Eric

  公开号：US09045524B2

  公开（公告）日：2015-06-02

  The present invention relates to compounds of Formula I, II, IVC, VIIIC, IXC, or XC and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds for the selective inhibition of one or more caspases. Also described are methods where the compounds of Formula I, II, IVC, VIIIC, IXC, or XC are used in the prevention and/or treatment of various diseases and conditions in subjects, including caspase-mediated diseases such as sepsis, myocardial infarction, ischemic stroke, spinal cord injury (SCI), traumatic brain injury (TBI) and neurodegenerative disease (e.g. multiple sclerosis (MS) and Alzheimer's, Parkinson's, and Huntington's diseases). Processes for synthesizing tripeptides are provided.

  本发明涉及公式I、II、IVC、VIIIC、IXC或XC化合物及其药物用途。本发明的特定方面涉及使用这些化合物选择性地抑制一个或多个半胱氨酸蛋白酶。还描述了使用公式I、II、IVC、VIIIC、IXC或XC化合物预防和/或治疗各种疾病和病症的方法，包括半胱氨酸蛋白酶介导的疾病，如败血症、心肌梗死、缺血性卒中、脊髓损伤、创伤性脑损伤和神经退行性疾病（例如多发性硬化症和阿尔茨海默病、帕金森病和亨廷顿病）。提供了三肽合成的方法。