diethyl ((S)-1-((R)-1-hydroxybutan-2-yl)aziridin-2-yl)phosphonate | 1309980-47-9

• 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 ((S)-1-((R)-1-hydroxybutan-2-yl)aziridin-2-yl)phosphonate
• 英文别名: (2R)-2-[(2S)-2-diethoxyphosphorylaziridin-1-yl]butan-1-ol
• CAS: 1309980-47-9
• 化学式: C₁₀H₂₂NO₄P
• 分子量: 251.263
• InChiKey: NLRLYGKBWJBYCI-JKIOLJMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl ((S)-1-((R)-1-hydroxybutan-2-yl)aziridin-2-yl)phosphonate 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.08h， 以87%的产率得到(R)-N-[(S)-2-chloro-1-(diethoxyphosphoryl)ethyl]-1-hydroxybutan-2-aminium chloride
  参考文献：
  名称：

  通过未活化的氮丙啶-2-膦酸酯的区域选择性开环合成β-氯-α-氨基膦酸酯衍生物

  摘要：

  摘要 通过改良的加布里埃尔-克伦威尔反应合成了一系列未活化的外消旋和手性氮丙啶-2-膦酸酯。合成的膦酸盐通过气态 HCl 的开环反应提供了广泛的生物学上有趣的新型 β-氯-α-氨基膦酸盐。针对上述每种产物的所有反应都可以以高产率区域选择性地进行。图形概要

  DOI：

  10.1080/10426507.2018.1513521
• 作为产物：
  描述：

  乙酰亚磷酸二乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 diethyl ((S)-1-((R)-1-hydroxybutan-2-yl)aziridin-2-yl)phosphonate
  参考文献：
  名称：

  New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes

  摘要：

  A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.005

文献信息

• Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives
  作者：Rehan Khan、Sinem Ulusan、Sreeparna Banerjee、Özdemir Dogan

  DOI：10.1002/cbdv.201900375

  日期：2019.11

  New aziridine 2-phosphonic acids were prepared by monohydrolysis of the aziridine 2-phosphonates that were obtained by the modified Gabriel-Cromwell reaction of vinyl phosphonate or α-tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT-116 colorectal cancer cell lines and the CCD-18Co normal colon fibroblast lines using

  通过将膦酸乙烯基酯或α-甲苯磺酰基乙烯基膦酸酯与伯胺或手性胺的改性Gabriel-Cromwell反应获得的氮丙啶2-膦酸酯单水解制备新的氮丙啶2-膦酸。使用MTT测定法测试了这些化合物对HCT-116结肠直肠癌细胞系和CCD-18Co正常结肠成纤维细胞系的细胞毒性。三种合成的膦酸衍生物2e（乙基氢（（2S）-1-[（1S）-1-（萘-2-基）乙基]叠氮吡啶-2-基}膦酸酯）2h（乙基氢（1-苄基氮丙啶-2-基）膦酸酯和2i（乙基氢（1-环己基氮丙啶-2-基）膦酸酯）显示出比参考癌症治疗药物依托泊苷更高的细胞毒性。细胞死亡是通过强烈诱导凋亡，甚至比依托泊苷更有效，
• New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes
  作者：Özdemir Dogan、Muhammet Isci、Muhittin Aygun

  DOI：10.1016/j.tetasy.2013.04.005

  日期：2013.5

  A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of <i>β</i>-chloro-<i>α</i>-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates
  作者：Sidika Polat-Cakir、Nurzhan Beksultanova、Özdemir Dogan

  DOI：10.1080/10426507.2018.1513521

  日期：2018.12.2

  Abstract A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel β-chloro-α-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields

  摘要 通过改良的加布里埃尔-克伦威尔反应合成了一系列未活化的外消旋和手性氮丙啶-2-膦酸酯。合成的膦酸盐通过气态 HCl 的开环反应提供了广泛的生物学上有趣的新型 β-氯-α-氨基膦酸盐。针对上述每种产物的所有反应都可以以高产率区域选择性地进行。图形概要