1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indol-9(6H)-one | 1403956-54-6

• 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: 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indol-9(6H)-one
• 英文别名: 1-(5-methylhexyl)-3,6,7,8-tetrahydro-2H-naphtho[2,1-e]indol-9-one
• CAS: 1403956-54-6
• 化学式: C₂₃H₂₉NO
• 分子量: 335.489
• InChiKey: KVDJPLMEBCTARW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(6-溴萘-2-基)甲烷磺酰胺 在 bis(triphenylphosphine)nickel(II) chloride 、 异丁酰胺 、 三氟化硼乙醚 、 sodium hydride 、 sodium cyanoborohydride 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 生成 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indol-9(6H)-one
  参考文献：
  名称：

  Synthesis and properties of two PRODAN-based fluorescent models of cholesterol

  摘要：

  The syntheses and photophysical properties of 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indo1-9(6H)-one (7a) and 1-(5-methylhexyl)-23,8,9-terrahydro-1H-naphrho[2,1-e]indol-6(7H)-one (7b) are reported. They are prepared in eight steps from the corresponding bromonaphthylamines. These fluorescent compounds have PRODAN-like cores, and they are structurally similar to cholesterol. Compound 7a is the first reported PRODAN derivative where both the amino and carbonyl groups are constrained to be coplanar with the naphthalene core. Comparing the photophysical behavior of these compounds with related compounds indicates that locking the amino group in a five-membered ring enhances their desirable properties as solvent polarity sensors. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.04.011

文献信息

• Synthesis and properties of two PRODAN-based fluorescent models of cholesterol
  作者：Nicholas A. Lopez、Christopher J. Abelt

  DOI：10.1016/j.jphotochem.2012.04.011

  日期：2012.6

  The syntheses and photophysical properties of 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indo1-9(6H)-one (7a) and 1-(5-methylhexyl)-23,8,9-terrahydro-1H-naphrho[2,1-e]indol-6(7H)-one (7b) are reported. They are prepared in eight steps from the corresponding bromonaphthylamines. These fluorescent compounds have PRODAN-like cores, and they are structurally similar to cholesterol. Compound 7a is the first reported PRODAN derivative where both the amino and carbonyl groups are constrained to be coplanar with the naphthalene core. Comparing the photophysical behavior of these compounds with related compounds indicates that locking the amino group in a five-membered ring enhances their desirable properties as solvent polarity sensors. (C) 2012 Elsevier B.V. All rights reserved.