ethyl 2-(2,2,2-trifluoroacetamido)-2,3-dihydro-(2-phenylpyrrol-3-ylidene)-5-methoxy-1H-indene-2-carboxylate | 1359680-75-3

• 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: ethyl 2-(2,2,2-trifluoroacetamido)-2,3-dihydro-(2-phenylpyrrol-3-ylidene)-5-methoxy-1H-indene-2-carboxylate
• 英文别名: ethyl 6-methoxy-3-(5-phenyl-2,3-dihydropyrrol-4-ylidene)-2-[(2,2,2-trifluoroacetyl)amino]-1H-indene-2-carboxylate
• CAS: 1359680-75-3
• 化学式: C₂₅H₂₃F₃N₂O₄
• 分子量: 472.464
• InChiKey: SJXDNDHCKBEPQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2,2,2-trifluoroacetamido)-2,3-dihydro-(2-phenylpyrrol-3-ylidene)-5-methoxy-1H-indene-2-carboxylate 、 三氟甲烷磺酸甲酯 以 苯 为溶剂， 以100%的产率得到ethyl 6-methoxy-3-(1-methyl-5-phenyl-2,3-dihydropyrrol-1-ium-4-ylidene)-2-[(2,2,2-trifluoroacetyl)amino]-1H-indene-2-carboxylate;trifluoromethanesulfonate
  参考文献：
  名称：

  Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain

  摘要：

  The N-alkylated indanylidenepyrroline (NAIP) Schiff base 3 is an unnatural a-amino acid precursor potentially useful for the preparation of semisynthetic peptides and proteins incorporating charged side chains whose structure can be modulated via Z/E photoisomerization. Here we report that the heteroallylic protons of 3 led to partial loss of ethanol accompanied by formation of the novel heterocyclic system 4 during attempted deprotection. We also show that the same protons catalyze the thermal isomerization of 3, making the light-driven conformational control concept ineffective for times longer than a few hours. These problems are not present in the previously unreported compound 5 where the acidic methyl group is replaced by an H atom. Therefore, 5, rather than 3, constitutes a promising prototype for the design of building blocks capable to modulate the electrostatic potential of a protein in specific locations via light irradiation.

  DOI：

  10.1021/jo2022263
• 作为产物：
  描述：

  ethyl 5-methoxy-1-oxo-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate 在 三氟甲磺酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 ethyl 2-(2,2,2-trifluoroacetamido)-2,3-dihydro-(2-phenylpyrrol-3-ylidene)-5-methoxy-1H-indene-2-carboxylate
  参考文献：
  名称：

  Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain

  摘要：

  The N-alkylated indanylidenepyrroline (NAIP) Schiff base 3 is an unnatural a-amino acid precursor potentially useful for the preparation of semisynthetic peptides and proteins incorporating charged side chains whose structure can be modulated via Z/E photoisomerization. Here we report that the heteroallylic protons of 3 led to partial loss of ethanol accompanied by formation of the novel heterocyclic system 4 during attempted deprotection. We also show that the same protons catalyze the thermal isomerization of 3, making the light-driven conformational control concept ineffective for times longer than a few hours. These problems are not present in the previously unreported compound 5 where the acidic methyl group is replaced by an H atom. Therefore, 5, rather than 3, constitutes a promising prototype for the design of building blocks capable to modulate the electrostatic potential of a protein in specific locations via light irradiation.

  DOI：

  10.1021/jo2022263