(4-叠氮基苯基)-[6-羟基-2-(4-羟基苯基)-1-苯并噻吩-3-基]甲酮 | 131589-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-叠氮基苯基)-[6-羟基-2-(4-羟基苯基)-1-苯并噻吩-3-基]甲酮
• 英文名称: 3-(4-Azidobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene
• 英文别名: (4-azidophenyl)-[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]methanone
• CAS: 131589-60-1
• 化学式: C₂₁H₁₃N₃O₃S
• 分子量: 387.419
• InChiKey: XBMPLXNNPNMNRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-叠氮基苯基)-[6-羟基-2-(4-羟基苯基)-1-苯并噻吩-3-基]甲酮 在 palladium/alumina 氢气 作用下， 以 乙酸乙酯 、 三乙胺 为溶剂， 反应 3.0h， 以92%的产率得到3-(4-氨基苯甲酰基)-6-羟基-2-(4-羟基苯基)-苯并[b]噻吩
  参考文献：
  名称：

  Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor

  摘要：

  A tetrafluoro-substituted aryl azide 1 and its protio analogue 2, both photoaffinity labeling reagents for the estrogen receptor, have been prepared by direct coupling of the appropriately substituted 4-azidobenzoyl chloride with the electron rich C-3 of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 3. This represents a rare example of aryl azide stability under Friedel-Crafts acylation conditions. Alternatively, the protio analogue 2 can also be prepared with the azide functionality masked as a phthaloyl-protected arylamine, and the tetrafluoro analogue 1, by direct displacement of a pentafluoroaryl derivative 20 with NaN3. Solution photolysis of tetrafluoro-substituted aryl azide (bis-methyl ether) 15 and its protio analogue 16 in toluene at 30-degrees-C results in relatively high yields of products derived from C-H insertion. Both azides 1 and 2 demonstrate favorable relative binding affinity (RBA) (1 = 10%, 2 = 66%, estradiol = 100%) and photoinactivation efficiency (1 = 43%, 2 = 55% at 30 min) for the estrogen receptor (ER). The synthesis of both azides has been modified to accommodate a palladium-catalyzed tritium gas hydrogenolysis of an iodoaryl precursor at a late stage in the synthetic sequence, as will be needed to prepare them in radiolabeled form, and this procedure has been verified by deuteration. This pair of compounds will allow a detailed evaluation of the role that fluorine substitution plays in the photochemistry and photocovalent attachment behavior of aryl azides in a complex biochemical system, the estrogen receptor. The radiosynthesis and further biochemical results will be presented elsewhere.

  DOI：

  10.1021/jo00009a037
• 作为产物：
  描述：

  4-叠氮基苯甲酰氯 在 三氟二甲基硫醚络合物 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 生成 (4-叠氮基苯基)-[6-羟基-2-(4-羟基苯基)-1-苯并噻吩-3-基]甲酮
  参考文献：
  名称：

  Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor

  摘要：

  A tetrafluoro-substituted aryl azide 1 and its protio analogue 2, both photoaffinity labeling reagents for the estrogen receptor, have been prepared by direct coupling of the appropriately substituted 4-azidobenzoyl chloride with the electron rich C-3 of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 3. This represents a rare example of aryl azide stability under Friedel-Crafts acylation conditions. Alternatively, the protio analogue 2 can also be prepared with the azide functionality masked as a phthaloyl-protected arylamine, and the tetrafluoro analogue 1, by direct displacement of a pentafluoroaryl derivative 20 with NaN3. Solution photolysis of tetrafluoro-substituted aryl azide (bis-methyl ether) 15 and its protio analogue 16 in toluene at 30-degrees-C results in relatively high yields of products derived from C-H insertion. Both azides 1 and 2 demonstrate favorable relative binding affinity (RBA) (1 = 10%, 2 = 66%, estradiol = 100%) and photoinactivation efficiency (1 = 43%, 2 = 55% at 30 min) for the estrogen receptor (ER). The synthesis of both azides has been modified to accommodate a palladium-catalyzed tritium gas hydrogenolysis of an iodoaryl precursor at a late stage in the synthetic sequence, as will be needed to prepare them in radiolabeled form, and this procedure has been verified by deuteration. This pair of compounds will allow a detailed evaluation of the role that fluorine substitution plays in the photochemistry and photocovalent attachment behavior of aryl azides in a complex biochemical system, the estrogen receptor. The radiosynthesis and further biochemical results will be presented elsewhere.

  DOI：

  10.1021/jo00009a037

文献信息

• Synthesis of a tetrafluoro-substituted aryl azide and its protio analog as photoaffinity labeling reagents for the estrogen receptor
  作者：Kevin G. Pinney、John A. Katzenellenbogen

  DOI：10.1021/jo00009a037

  日期：1991.4

  A tetrafluoro-substituted aryl azide 1 and its protio analogue 2, both photoaffinity labeling reagents for the estrogen receptor, have been prepared by direct coupling of the appropriately substituted 4-azidobenzoyl chloride with the electron rich C-3 of 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 3. This represents a rare example of aryl azide stability under Friedel-Crafts acylation conditions. Alternatively, the protio analogue 2 can also be prepared with the azide functionality masked as a phthaloyl-protected arylamine, and the tetrafluoro analogue 1, by direct displacement of a pentafluoroaryl derivative 20 with NaN3. Solution photolysis of tetrafluoro-substituted aryl azide (bis-methyl ether) 15 and its protio analogue 16 in toluene at 30-degrees-C results in relatively high yields of products derived from C-H insertion. Both azides 1 and 2 demonstrate favorable relative binding affinity (RBA) (1 = 10%, 2 = 66%, estradiol = 100%) and photoinactivation efficiency (1 = 43%, 2 = 55% at 30 min) for the estrogen receptor (ER). The synthesis of both azides has been modified to accommodate a palladium-catalyzed tritium gas hydrogenolysis of an iodoaryl precursor at a late stage in the synthetic sequence, as will be needed to prepare them in radiolabeled form, and this procedure has been verified by deuteration. This pair of compounds will allow a detailed evaluation of the role that fluorine substitution plays in the photochemistry and photocovalent attachment behavior of aryl azides in a complex biochemical system, the estrogen receptor. The radiosynthesis and further biochemical results will be presented elsewhere.