(R)-2-Bromo-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid | 439089-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-Bromo-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid
• 英文别名: (2R)-2-bromo-5-[(2,2,2-trifluoroacetyl)amino]pentanoic acid
• CAS: 439089-65-3
• 化学式: C₇H₉BrF₃NO₃
• 分子量: 292.053
• InChiKey: BRGHRTICQYEKLV-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-Bromo-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid 在 dipotassium hydrogenphosphate 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-[[(R)-2-Bromo-5-(2,2,2-trifluoro-acetylamino)-pentanoyl]-(2,4-dimethoxy-benzyl)-amino]-malonic acid dimethyl ester
  参考文献：
  名称：

  A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor

  摘要：

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.

  DOI：

  10.1021/jo010757o
• 作为产物：
  描述：

  (R)-2-Amino-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid 在 硫酸 、 potassium bromide 、 sodium nitrite 作用下， 反应 4.0h， 以74%的产率得到(R)-2-Bromo-5-(2,2,2-trifluoro-acetylamino)-pentanoic acid
  参考文献：
  名称：

  A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor

  摘要：

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.

  DOI：

  10.1021/jo010757o

文献信息

• A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor
  作者：Xinhua Qian、Bin Zheng、Brian Burke、Manohar T. Saindane、David R. Kronenthal

  DOI：10.1021/jo010757o

  日期：2002.5.1

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.