1-hydrazide 3α-amino-7α,12α-di(1-pyrenebutanoyl)-5β-cholan-24-oate | 917595-43-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-hydrazide 3α-amino-7α,12α-di(1-pyrenebutanoyl)-5β-cholan-24-oate
• CAS: 917595-43-8
• 化学式: C₆₄H₇₁N₃O₅
• 分子量: 962.285
• InChiKey: IGPQDXOJKIGZIW-IKXVWUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.26
• 重原子数：
  72.0
• 可旋转键数：
  14.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  133.74
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-hydrazide 3α-amino-7α,12α-di(1-pyrenebutanoyl)-5β-cholan-24-oate 、 4-(三氟甲基)异硫氰酸苯酯 以 二氯甲烷 为溶剂， 反应 36.0h， 以29%的产率得到1-[(4'-trifluoromethylphenyl)thioureido]hydrazide 3α-[(4'trifluoromethylphenyl)thioureido]-7α,12α-di(1-pyrenebutanoyl)-5β-cholan-24-oate
  参考文献：
  名称：

  Cholic acid-based high sensitivity fluorescent sensor for α,ω-dicarboxylate: an intramolecular excimer emission quenched by complexation

  摘要：

  Fluorescent receptors (1 and 2) bearing two binding units on C3 and C24 and two signal display units on C7 and C12 of cholic acid, respectively, were designed and synthesized. Both I and 2 emit a much weaker fluorescence than that of the control compound 3 lacking of the binding units reflecting that a PET process originated from the C-3 thiourea group to the plural pyrenyl pendant groups is operative. Addition of terminal dicarboxylate anions to the CH3CN solution of 1 or 2 enhances the PET process, which leads to a significant and highly sensitive fluorescence response, resulting in an almost complete quenching of the excimer emission of the signal units. To maximize the interaction of the host and the guest, carboxylates of more than five carbon chains could penetrate through the space between the two pyrenyl pendants of the host, triggering a considerable conformational change of the fluorophores. As a result, an enhancement of the monomer emission at the expense of the excimer emission will take place. The binding properties and mechanism of 1 and 2 to dicarboxylates in CH3CN were manifested by the combined fluorescence, UV-vis, and H-1 NMR spectroscopic method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.042
• 作为产物：
  描述：

  1-芘丁酸 在 磺酰氯 、 calcium hydride 、 苄基三乙基氯化铵 、 一水合肼 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 xylene 、 苯 为溶剂， 反应 96.0h， 生成 1-hydrazide 3α-amino-7α,12α-di(1-pyrenebutanoyl)-5β-cholan-24-oate
  参考文献：
  名称：

  Cholic acid-based high sensitivity fluorescent sensor for α,ω-dicarboxylate: an intramolecular excimer emission quenched by complexation

  摘要：

  Fluorescent receptors (1 and 2) bearing two binding units on C3 and C24 and two signal display units on C7 and C12 of cholic acid, respectively, were designed and synthesized. Both I and 2 emit a much weaker fluorescence than that of the control compound 3 lacking of the binding units reflecting that a PET process originated from the C-3 thiourea group to the plural pyrenyl pendant groups is operative. Addition of terminal dicarboxylate anions to the CH3CN solution of 1 or 2 enhances the PET process, which leads to a significant and highly sensitive fluorescence response, resulting in an almost complete quenching of the excimer emission of the signal units. To maximize the interaction of the host and the guest, carboxylates of more than five carbon chains could penetrate through the space between the two pyrenyl pendants of the host, triggering a considerable conformational change of the fluorophores. As a result, an enhancement of the monomer emission at the expense of the excimer emission will take place. The binding properties and mechanism of 1 and 2 to dicarboxylates in CH3CN were manifested by the combined fluorescence, UV-vis, and H-1 NMR spectroscopic method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.042