2-bromo-propionic acid dibutylamide | 81042-10-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-bromo-propionic acid dibutylamide
• 英文别名: N.N-Dibutyl-2-brom-propionamid；2-Brom-propionsaeure-dibutylamid；Propanamide, N,N-dibutyl-2-bromo-；2-bromo-N,N-dibutylpropanamide
• CAS: 81042-10-6
• 化学式: C₁₁H₂₂BrNO
• 分子量: 264.206
• InChiKey: YODUIZXBBCYMFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-propionic acid dibutylamide 、 4-叔丁基苯乙烯 在 叔丁基过氧化氢 、 三乙胺 、 cobalt acetylacetonate 作用下， 以 水 为溶剂， 反应 24.0h， 以61%的产率得到N,N-dibutyl-4-(4-(tert-butyl)phenyl)-2-methyl-4-oxobutanamide
  参考文献：
  名称：

  Co-Catalyzed Synthesis of 1,4-Dicarbonyl Compounds Using TBHP Oxidant

  摘要：

  A Co-catalyzed reaction for the construction of 1,4-dicarbonyls has been reported in which cascade organo-cobalt addition/trapping/Kornblum-DeLaMare rearrangement were involved. In view of the easy availability of starting materials, wide substrate scope, high functionality tolerance, and operational simplicity, this protocol constituted a simple, practical, and powerful alternative compared with previous approaches.

  DOI：

  10.1021/ol5004687

文献信息

• 2,4-Diarylpyrrolidine-3-carboxylic AcidsPotent ET_A Selective Endothelin Receptor Antagonists. 1. Discovery of A-127722
  作者：Martin Winn、Thomas W. von Geldern、Terry J. Opgenorth、Hwan-Soo Jae、Andrew S. Tasker、Steven A. Boyd、Jeffrey A. Kester、Robert A. Mantei、Radhika Bal、Bryan K. Sorensen、Jinshyun R. Wu-Wong、William J. Chiou、Douglas B. Dixon、Eugene I. Novosad、Lisa Hernandez、Kennan C. Marsh

  DOI：10.1021/jm9505369

  日期：1996.1.1

  We have discovered a novel class of endothelin (ET) receptor antagonists through pharmacophore analysis of the existing non-peptide ET antagonists. On the basis of this analysis, we determined that a pyrrolidine ring might replace the indan ring in SE 209670. The resultant compounds were readily prepared and amenable to extensive SAR studies. Thus a series of N-substituted trans,trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl) pyrrolidine-3-carboxylic acids (8) have been synthesized and evaluated for binding at ET(A) and ET(B) receptors. Compounds with N-acyl and simple N-alkyl substituents had weak activity. Compounds with N-alkyl substituents containing ethers, sulfoxides, or sulfones showed increased activity. Much improved activity resulted from compounds where the N-substituents were acetamides. Compound 17u (A-127722) with the N,N-dibutylacetamide substituent is the best of the series. It has an IC50 = 0.36 nM for inhibition of ET-1 radioligand binding at the ETA(A) receptor, with a 1000-fold selectivity for the ET(A) vs the ET(B) receptor. It is also a potent inhibitor (IC50 = 0.16 nM) of phosphoinositol hydrolysis stimulated by ET-1, and it antagonized the ET-l-induced contraction of the rabbit aorta with a pA(2) = 9.20. The compound has 70% oral bioavailability in rats.
• Co-Catalyzed Synthesis of 1,4-Dicarbonyl Compounds Using TBHP Oxidant
  作者：Feng Zhang、Peng Du、Jijun Chen、Hongxiang Wang、Qiang Luo、Xiaobing Wan

  DOI：10.1021/ol5004687

  日期：2014.4.4

  A Co-catalyzed reaction for the construction of 1,4-dicarbonyls has been reported in which cascade organo-cobalt addition/trapping/Kornblum-DeLaMare rearrangement were involved. In view of the easy availability of starting materials, wide substrate scope, high functionality tolerance, and operational simplicity, this protocol constituted a simple, practical, and powerful alternative compared with previous approaches.