5'-methoxy-2',2'-dimethyl-3-oxaspiro[bicyclo[3.1.0]hexane-2-indan]-4-one | 1235574-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5'-methoxy-2',2'-dimethyl-3-oxaspiro[bicyclo[3.1.0]hexane-2-indan]-4-one
• CAS: 1235574-87-4
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: XNNGHHNYWXQLDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5'-methoxy-2',2'-dimethyl-3-oxaspiro[bicyclo[3.1.0]hexane-2-indan]-4-one 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以93%的产率得到2-bromo-4-(5-methoxy-2,2-dimethylindan-1-ylidene)butyric acid
  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：

  5-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one 、 ethyl (1S,2S)-2-iodocyclopropanecarboxylate 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到5'-methoxy-2',2'-dimethyl-3-oxaspiro[bicyclo[3.1.0]hexane-2-indan]-4-one
  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