{(S)-2-Isobutyl-4-[(R)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde | 454180-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: {(S)-2-Isobutyl-4-[(R)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde
• 英文别名: 2-[(2S)-2-(2-methylpropyl)-3-oxo-4-[(2R)-1-(2-trimethylsilylethoxymethoxy)propan-2-yl]-1H-pyrrol-2-yl]acetaldehyde
• CAS: 454180-53-1
• 化学式: C₁₉H₃₅NO₄Si
• 分子量: 369.577
• InChiKey: SMRCVKRWZVBNEW-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {(S)-2-Isobutyl-4-[(R)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde 在 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.25h， 生成 (2S,5'S)-4-((R)-1-Carboxy-ethyl)-5'-(2,2-dimethoxy-ethyl)-2,5'-diisobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid dibenzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Pyrrolinone-Based Matrix Metalloprotease Inhibitor

  摘要：

  [GRAPHICS]A pyrrolinone-based hydroxamate matrix metalloprotease inhibitor, (-)-1, has been designed and synthesized. Enzymatic assay revealed that (-)-1 inhibited three of the ten matrix metalloprotease enzymes examined and as such represents a new, potentially important lead structure.

  DOI：

  10.1021/ol000254p
• 作为产物：
  描述：

  (S)-2-(2,2-Dimethoxy-ethyl)-2-isobutyl-4-[(R)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-1,2-dihydro-pyrrol-3-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以99%的产率得到{(S)-2-Isobutyl-4-[(R)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Pyrrolinone-Based Matrix Metalloprotease Inhibitor

  摘要：

  [GRAPHICS]A pyrrolinone-based hydroxamate matrix metalloprotease inhibitor, (-)-1, has been designed and synthesized. Enzymatic assay revealed that (-)-1 inhibited three of the ten matrix metalloprotease enzymes examined and as such represents a new, potentially important lead structure.

  DOI：

  10.1021/ol000254p

文献信息

• Design, Synthesis, and Evaluation of a Pyrrolinone-Based Matrix Metalloprotease Inhibitor
  作者：Amos B. Smith、Thomas Nittoli、Paul A. Sprengeler、James J.-W. Duan、Rui-Qin Liu、Ralph F. Hirschmann

  DOI：10.1021/ol000254p

  日期：2000.11.1

  [GRAPHICS]A pyrrolinone-based hydroxamate matrix metalloprotease inhibitor, (-)-1, has been designed and synthesized. Enzymatic assay revealed that (-)-1 inhibited three of the ten matrix metalloprotease enzymes examined and as such represents a new, potentially important lead structure.