(R)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (3-bromophenyl)carbamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (3-bromophenyl)carbamate
• 英文别名: 2-[(3R)-4-methylidene-5-oxooxolan-3-yl]ethyl N-(3-bromophenyl)carbamate
• 化学式: C₁₄H₁₄BrNO₄
• 分子量: 340.173
• InChiKey: SVHBYYYYWSNSKE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cis-4-hydroxybut-2-en-1-ylprop-2-ynoate 在 silver hexafluoroantimonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 硼烷四氢呋喃络合物 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 22.17h， 生成 (R)-2-(4-methylene-5-oxotetrahydrofuran-3-yl)ethyl (3-bromophenyl)carbamate
  参考文献：
  名称：

  Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages

  摘要：

  A series of new alpha-methylene-gamma-lactone carbamates were synthesized by an asymmetric synthetic route. The activities on inhibiting nitric oxide (NO) release of these compounds were evaluated in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. The results indicated that most of the compounds except one exhibited potent NO inhibitory effect with IC50 value more than 2 mu M. The cytotoxicities of these compounds were estimated via MTT assays. The results suggested that six compounds were accompanied by low cytotoxicity. The structure activity relationships were also discussed. The S configuration of C3 on lactones ring would be more helpful to NO inhibitory effect. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.016

文献信息

• Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages
  作者：Wen-Hao Shao、Bing-Yang Chen、Xiang-Rong Cheng、Hu Yuan、Hao Chen、Wan-Lin Chang、Ji Ye、Shan Lin、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1016/j.ejmech.2015.02.016

  日期：2015.3

  A series of new alpha-methylene-gamma-lactone carbamates were synthesized by an asymmetric synthetic route. The activities on inhibiting nitric oxide (NO) release of these compounds were evaluated in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. The results indicated that most of the compounds except one exhibited potent NO inhibitory effect with IC50 value more than 2 mu M. The cytotoxicities of these compounds were estimated via MTT assays. The results suggested that six compounds were accompanied by low cytotoxicity. The structure activity relationships were also discussed. The S configuration of C3 on lactones ring would be more helpful to NO inhibitory effect. (C) 2015 Elsevier Masson SAS. All rights reserved.