4-(5-methoxy-2,2-dimethylindan-1-ylidene)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester | 1235574-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(5-methoxy-2,2-dimethylindan-1-ylidene)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester
• CAS: 1235574-95-4
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: ILETWEMWFFCYNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(5-methoxy-2,2-dimethylindan-1-ylidene)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester 、 三氟甲烷磺酸甲酯 以 苯 为溶剂， 反应 2.0h， 生成 4-(5-methoxy-2,2-dimethylindan-1-ylidene)-2-(methoxycarbonyl)-1,5-dimethyl-3,4-dihydro-2H-pyrrolium trifluoromethanesulfonate
  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
• 作为产物：
  描述：

  2-acetamido-4-(5-methoxy-2,2-dimethylindan-1-ylidene)butyric acid methyl ester 在 六甲基二硅氧烷 、 四磷十氧化物 作用下， 以 四氯化碳 为溶剂， 以46%的产率得到4-(5-methoxy-2,2-dimethylindan-1-ylidene)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid methyl ester
  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