diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate | 66932-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate
• 英文别名: 2-Di(propan-2-yloxy)phosphoryl-1-pyrrolidin-1-ylethanone
• CAS: 66932-77-2
• 化学式: C₁₂H₂₄NO₄P
• 分子量: 277.301
• InChiKey: AIWIFAKUOIHUFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对叔丁基苯甲醛 、 吉拉尔特试剂 T 、 diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以99%的产率得到3-(4-Tert-butylphenyl)-1-pyrrolidin-1-ylprop-2-en-1-one
  参考文献：
  名称：

  Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library

  摘要：

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.

  DOI：

  10.1021/co400003d
• 作为产物：
  描述：

  四氢吡咯 、 diisopropyl (methoxycarbonylmethyl)phosphonate 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以60%的产率得到diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate
  参考文献：
  名称：

  膦酰基乙酸酯的有效酯交换反应

  摘要：

  已开发出一种使用4-DMAP催化的酯交换反应制备差异取代的膦酰基乙酸酯和膦酰基乙酰胺的新方法。

  DOI：

  10.1016/s0040-4039(00)96188-4

文献信息

• HATAKEYAMA, SUSUMI;SATON, KUMIKO;SAKURAI, KUNIYA;TAKANO, SEIICHI, TETRAHEDRON. LETT., 28,(1987) N 24, 2713-2716
  作者：HATAKEYAMA, SUSUMI、SATON, KUMIKO、SAKURAI, KUNIYA、TAKANO, SEIICHI

  DOI：——

  日期：——
• Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library
  作者：Sumin Kim、Chaemin Lim、Sukjin Lee、Seokwoo Lee、Hyunkyung Cho、Joo-Youn Lee、Dong Sup Shim、Hee Dong Park、Sanghee Kim

  DOI：10.1021/co400003d

  日期：2013.4.8

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.
• Efficient ester exchange reaction of phosphonoacetates
  作者：Susumi Hatakeyama、Kumiko Satoh、Kuniya Sakurai、Seiichi Takano

  DOI：10.1016/s0040-4039(00)96188-4

  日期：1987.1

  A novel method for the preparation of differentially substituted phosphonoacetates and phosphonoacetamides using 4-DMAP catalyzed ester exchange reaction has been developed.

  已开发出一种使用4-DMAP催化的酯交换反应制备差异取代的膦酰基乙酸酯和膦酰基乙酰胺的新方法。