2,2,2-trifluoro-N-(8-methoxy-5-oxo-1,2,3,5,5 a,6-hexahydroindeno[1,2-e]indol-5a-yl)acetamide | 1359680-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,2,2-trifluoro-N-(8-methoxy-5-oxo-1,2,3,5,5 a,6-hexahydroindeno[1,2-e]indol-5a-yl)acetamide
• 英文别名: 2,2,2-trifluoro-N-(8-methoxy-5-oxo-1,2,3,6-tetrahydroindeno[1,2-e]indol-5a-yl)acetamide
• CAS: 1359680-73-1
• 化学式: C₁₈H₁₅F₃N₂O₃
• 分子量: 364.324
• InChiKey: VJZOWFJJUQZZBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 5-methoxy-1-(5-methyl-2H-pyrrol-4(3H)-ylidene)-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate 以 氘代氯仿 为溶剂， 生成 2,2,2-trifluoro-N-(8-methoxy-5-oxo-1,2,3,5,5 a,6-hexahydroindeno[1,2-e]indol-5a-yl)acetamide
  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.