methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | 1267907-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
• 英文别名: Methyl 2-[5-methoxy-2-methyl-1-(2,4,6-trichlorobenzoyl)indol-3-yl]acetate；methyl 2-[5-methoxy-2-methyl-1-(2,4,6-trichlorobenzoyl)indol-3-yl]acetate
• CAS: 1267907-58-3
• 化学式: C₂₀H₁₆Cl₃NO₄
• 分子量: 440.71
• InChiKey: UTLSITCLWDUNJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以73%的产率得到5-methoxy-2-methyl-1-(2,4,6-trichlorobenzoyl)-1H-indole-3-acetic acid
  参考文献：
  名称：

  Atropisomerism Observed in Indometacin Derivatives

  摘要：

  To elucidate the active conformation of indometacin that differentiates between cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), the stereochemistry around the N-benzoylated indole moiety of indometacin was studied. Resolution of stable atropisomers as representative conformations was found to be possible by restricting rotation about the N-C7' and/or C7'-C1' bond. Only the aR-isomer showed specific inhibition of COX-1, and COX-2 was not inhibited by either atropisomer.

  DOI：

  10.1021/ol103008d
• 作为产物：
  描述：

  2,4,6-三氯苯甲酰氯 、 5-甲氧基-2-甲基-3-吲哚乙酸甲酯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.08h， 以95%的产率得到methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
  参考文献：
  名称：

  Atropisomerism Observed in Indometacin Derivatives

  摘要：

  To elucidate the active conformation of indometacin that differentiates between cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), the stereochemistry around the N-benzoylated indole moiety of indometacin was studied. Resolution of stable atropisomers as representative conformations was found to be possible by restricting rotation about the N-C7' and/or C7'-C1' bond. Only the aR-isomer showed specific inhibition of COX-1, and COX-2 was not inhibited by either atropisomer.

  DOI：

  10.1021/ol103008d

文献信息

• Atropisomerism Observed in Indometacin Derivatives
  作者：Hideyo Takahashi、Shintaro Wakamatsu、Hidetsugu Tabata、Tetsuta Oshitari、Ayako Harada、Keizo Inoue、Hideaki Natsugari

  DOI：10.1021/ol103008d

  日期：2011.2.18

  To elucidate the active conformation of indometacin that differentiates between cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), the stereochemistry around the N-benzoylated indole moiety of indometacin was studied. Resolution of stable atropisomers as representative conformations was found to be possible by restricting rotation about the N-C7' and/or C7'-C1' bond. Only the aR-isomer showed specific inhibition of COX-1, and COX-2 was not inhibited by either atropisomer.