diisopropyl [(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phosphonate | 51814-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diisopropyl [(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phosphonate
• 英文别名: dipropan-2-yl [(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phosphonate；phthalimidomethyl-phosphonic acid diisopropyl ester；2-[di(propan-2-yloxy)phosphorylmethyl]isoindole-1,3-dione
• CAS: 51814-62-1
• 化学式: C₁₅H₂₀NO₅P
• 分子量: 325.301
• InChiKey: LMIQWVVDMSNPNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diisopropyl [(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phosphonate 反应 0.5h， 以63%的产率得到N-甲基邻苯二甲酰亚胺
  参考文献：
  名称：

  Efficient synthesis routes for various phthalimido phosphor esters as antimicrobial agents in terms of structure–activity relationship

  摘要：

  A series of phthalimido phosphor derivatives-alpha-amino-phosphonates, amidophosphonates, phosphonic acid diamides, and oxadiazaphospholes-were prepared by applying different types of phosphorus(III) reagents to 2-methoxy-1H-isoindole-1,3(2H)-dione and 2-anilino-1H-isoindole-1,3(2H)-dione. On the basis of bioassay results, some of the new phosphoryl imides could be considered as lead molecules to be modified in order to improve their antibiotic activity.

  DOI：

  10.1007/s00706-009-0244-1
• 作为产物：
  描述：

  N-甲氧基邻苯二甲酰亚胺 、 三异丙基亚磷酸酯 反应 20.0h， 以77%的产率得到diisopropyl [(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phosphonate
  参考文献：
  名称：

  Efficient synthesis routes for various phthalimido phosphor esters as antimicrobial agents in terms of structure–activity relationship

  摘要：

  A series of phthalimido phosphor derivatives-alpha-amino-phosphonates, amidophosphonates, phosphonic acid diamides, and oxadiazaphospholes-were prepared by applying different types of phosphorus(III) reagents to 2-methoxy-1H-isoindole-1,3(2H)-dione and 2-anilino-1H-isoindole-1,3(2H)-dione. On the basis of bioassay results, some of the new phosphoryl imides could be considered as lead molecules to be modified in order to improve their antibiotic activity.

  DOI：

  10.1007/s00706-009-0244-1

文献信息

• Silver-Catalyzed Ring Expansion of Activated N-Heteroarenes via 1,4-Dearomative Addition of Diazomethylphosphonates
  作者：Sekwang Baek、Hyundug Jen、Eun Jeong Yoo

  DOI：10.1055/a-2004-1279

  日期：2023.4

  phosphorus-containing azepine derivatives via a domino-type dearomatization procedure, followed by ring expansion. In addition, diazomethylphosphonates were employed for the first time as nucleophiles in the 1,4-dearomative addition of activated N-heteroarenes, furnishing cyclopropane-fused piperidine intermediates that were readily restructured into their corresponding azepine derivatives. The reactivities

  含磷氮杂环由于其独特的结构特征和生物活性而成为重要的分子基序。在这项研究中，我们开发了一种银催化反应，通过多米诺型脱芳构化程序构建含磷氮杂庚因衍生物，然后进行扩环。此外，重氮甲基膦酸酯首次在活化的 N-杂芳烃的 1,4-脱芳烃加成反应中用作亲核试剂，提供环丙烷稠合的哌啶中间体，这些中间体很容易重组为相应的吖庚因衍生物。发现重氮甲基膦酸酯在开发的脱芳构化策略中的反应性优于其他重氮化合物，
• Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines
  作者：Wenlai Xie、Chengzhuo Wang、Jiaxi Xu

  DOI：10.1021/acs.orglett.4c00881

  日期：2024.4.26

  s is achieved efficiently through the microwave-assisted reaction with phosphoryl diazomethanes. Both trialkyl and triaryl 1,3,5-triazinanes were converted by diazomethyldiarylphosphine oxides, dialkyl diazomethylphosphonates, and alkyl diazomethyl(aryl)phosphinates and functionalized simultaneously in good to excellent yields. The reaction is a sequence of 1,3,5-triazinane fragmentation, tandem nucleophilic

  通过与磷酰重氮甲烷的微波辅助反应，可以有效地将 1,3,5-三嗪转化为 5-磷酰基-1,2,3,4-四氢嘧啶。三烷基和三芳基1,3,5-三嗪烷均可通过重氮甲基二芳基氧化膦、重氮甲基膦酸二烷基酯和重氮甲基（芳基）次膦酸烷基酯转化并同时官能化，收率良好至优异。该反应是一系列 1,3,5-三嗪烷断裂、生成的福尔马亚胺和磷酰重氮甲烷的串联亲核加成，以及最终的N , N-缩醛化。