(Z)-4-(2-(ethoxycarbonyl)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium trifluoromethanesulfonate | 1359680-65-1

• 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: (Z)-4-(2-(ethoxycarbonyl)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium trifluoromethanesulfonate
• 英文别名: ethyl (3Z)-6-methoxy-3-(1-methyl-2,3-dihydropyrrol-1-ium-4-ylidene)-2-[(2,2,2-trifluoroacetyl)amino]-1H-indene-2-carboxylate;trifluoromethanesulfonate
• CAS: 1359680-65-1
• 化学式: CF₃O₃S*C₂₀H₂₂F₃N₂O₄
• 分子量: 560.471
• InChiKey: BMVHCLCMGSAIBE-PXJKFVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (Z)-4-(2-(ethoxycarbonyl)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium trifluoromethanesulfonate 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 (E)-4-(2-(ethoxycarbonyl)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium 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：

  在 4-二甲氨基吡啶 、 三氟甲磺酸 、 三氟甲磺酸酐 、 二异丁基氢化铝 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 (Z)-4-(2-(ethoxycarbonyl)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-inden-1-ylidene)-1-methyl-3,4-dihydro-2H-pyrrolium 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

文献信息

• Toward a Stable α-Cycloalkyl Amino Acid with a Photoswitchable Cationic Side Chain
  作者：Riccardo Rossi Paccani、Donato Donati、Stefania Fusi、Loredana Latterini、Grazia Farina、Vinicio Zanirato、Massimo Olivucci

  DOI：10.1021/jo2022263

  日期：2012.2.17

  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.