2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate | 1426294-34-9

• 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: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-di(propan-2-yloxy)phosphorylpropanoate；(2,5-dioxopyrrolidin-1-yl) 2-di(propan-2-yloxy)phosphorylpropanoate
• CAS: 1426294-34-9
• 化学式: C₁₃H₂₂NO₇P
• 分子量: 335.294
• InChiKey: IBHYRVHVRDXKJI-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±47.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate 、 吉拉尔特试剂 T 、 3,4-二甲氧基苯乙胺 以 二氯甲烷 、 甲醇 为溶剂， 反应 4.0h， 以99%的产率得到diisopropyl (1-((3,4-dimethoxyphenethyl)amino)-1-oxopropan-2-yl)phosphonate
  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：

  ethyl 2-(diisopropylphosphono)propionate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate
  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

文献信息

• [EN] PIPER AMIDE-BASED COMPOUND AS BOMBESIN RECEPTOR SUBTYPE 3<br/>[FR] COMPOSÉ À BASE D'AMIDE DE LA PLANTE DU GENRE PIPER UTILISÉ COMME RÉCEPTEUR DE BOMBÉSINE DE SOUS-TYPE 3
  申请人：SNU R&DB FOUNDATION

  公开号：WO2014129874A1

  公开（公告）日：2014-08-28

  본 발명은 신규한 α,β-불포화 아미드 화합물; 하나 이상의 α,β-불포화 아미드 화합물을 포함하는 화합물 라이브러리로부터 비만 예방 또는 치료효과를 나타내는 화합물을 선별하는 단계 및 상기 선별된 화합물을 함유하는 비만 예방 또는 치료용 조성물을 제조하는 단계를 포함하는 것이 특징인 비만 예방 또는 치료용 조성물 제조 방법; 및 α,β-불포화 아미드 화합물을 포함하는 비만 예방 또는 치료용 조성물에 관한 것이다. 본 발명의 α,β-불포화 아미드 화합물은 다양한 활성을 나타내는 천연물인 파이퍼 아미드를 모방하는 모핵구조를 가지는 화합물로서 다양한 약리활성을 나타낼 수 있을 것이며, 중간 산물로서 β-포스포노-N-히드록시숙신이미딜 에스테르(β-phosphono-N-hydroxysuccinimidyl ester)를 이용하여 가용성 부산물(by-products)을 생성하므로 통상적으로 이용되는 컬럼 크로마토그래피 정제과정을 수행할 필요없이 순수한 화합물을 획득할 수 있다. 또한 이렇게 합성된 화합물 라이브러리로부터 약리활성을 테스트하여 BRS-3에 대한 작용제인 화합물들을 스크리닝하여 비만 예방 또는 치료용 조성물로 유용하게 활용할 수 있다.
• 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.