ethyl 5-methoxy-1-(5-methyl-2H-pyrrol-4(3H)-ylidene)-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate | 1235575-01-5

• 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 5-methoxy-1-(5-methyl-2H-pyrrol-4(3H)-ylidene)-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: ethyl 6-methoxy-3-(5-methyl-2,3-dihydropyrrol-4-ylidene)-2-[(2,2,2-trifluoroacetyl)amino]-1H-indene-2-carboxylate
• CAS: 1235575-01-5
• 化学式: C₂₀H₂₁F₃N₂O₄
• 分子量: 410.393
• InChiKey: OLUNSTBQJXDFLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  ethyl 1-(3-acetamidopropylidene)-5-methoxy-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate 在 trimethylsilyl polyphosphate 作用下， 以63%的产率得到ethyl 5-methoxy-1-(5-methyl-2H-pyrrol-4(3H)-ylidene)-2-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Modeling, Preparation, and Characterization of a Dipole Moment Switch Driven by Z/E Photoisomerization

  摘要：

  We report the results of a multidisciplinary research effort where the methods of computational photochemistry and retrosynthetic analysis/synthesis have contributed to the preparation of a novel N-alkylated indanylidene-pyrroline Schiff base featuring an exocyclic double bond and a permanent zwitterionic head. We show that, due to its large dipole moment and efficient photoisomerization, such a system may constitute the prototype of a novel generation of electrostatic switches achieving a reversible light-induced dipole moment change on the order of 30 D. The modeling of a peptide fragment incorporating the zwitterionic head into a conformationally rigid side chain shows that the switch can effectively modulate the fluorescence of a tryptophan probe.

  DOI：

  10.1021/ja906733q