Phosphoric acid 2,2-diphenyl-ethyl ester bis-(4-nitro-phenyl) ester | 906072-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phosphoric acid 2,2-diphenyl-ethyl ester bis-(4-nitro-phenyl) ester
• CAS: 906072-79-5
• 化学式: C₂₆H₂₁N₂O₈P
• 分子量: 520.435
• InChiKey: JEKDBTHEKQFUPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  131.04
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid 2,2-diphenyl-ethyl ester bis-(4-nitro-phenyl) ester 在 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 反应 4.33h， 生成 bis-N,N-(2,2-diphenylethyl-12-aminododecyl phosphate)fumaramide
  参考文献：
  名称：

  Bolaamphiphiles Promote Phospholipid Translocation Across Vesicle Membranes

  摘要：

  A series of membrane-spanning bolaamphiphiles (molecules with two hydrophilic end groups connected by a hydrophobic linker) were prepared by a modular synthetic method and evaluated for their abilities to affect the dynamics of a surrounding bilayer membrane. The goal was to determine if the bolaamphiphiles promote the translocation of phospholipids across vesicle membranes. The bolaamphiphiles were incorporated at low levels (up to 5 mol %) in vesicles composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). Inward translocation assays were performed using fluorescent, NBD-labeled phospholipid probes with phosphocholine (PC) or phosphoglycerol (PG) headgroups. The membrane-spanning bolaamphiphiles promote the translocation of both phospholipid probes in the order PG > PC, whereas shorter bolaamphiphiles (structures that must adopt a U-shape and keep both end groups in the same leaflet of the membrane), and regular amphiphiles with one hydrophilic end group, are inactive. These results are an exception to the rule-of-thumb that membrane-spanning bolaamphiphiles are inherently membrane-stabilizing molecules that inhibit all types of membrane transport.

  DOI：

  10.1021/ja0619253
• 作为产物：
  描述：

  三(4-硝基苯基)磷酸酯 、 2,2-二苯基乙醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以90%的产率得到Phosphoric acid 2,2-diphenyl-ethyl ester bis-(4-nitro-phenyl) ester
  参考文献：
  名称：

  Bolaamphiphiles Promote Phospholipid Translocation Across Vesicle Membranes

  摘要：

  A series of membrane-spanning bolaamphiphiles (molecules with two hydrophilic end groups connected by a hydrophobic linker) were prepared by a modular synthetic method and evaluated for their abilities to affect the dynamics of a surrounding bilayer membrane. The goal was to determine if the bolaamphiphiles promote the translocation of phospholipids across vesicle membranes. The bolaamphiphiles were incorporated at low levels (up to 5 mol %) in vesicles composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). Inward translocation assays were performed using fluorescent, NBD-labeled phospholipid probes with phosphocholine (PC) or phosphoglycerol (PG) headgroups. The membrane-spanning bolaamphiphiles promote the translocation of both phospholipid probes in the order PG > PC, whereas shorter bolaamphiphiles (structures that must adopt a U-shape and keep both end groups in the same leaflet of the membrane), and regular amphiphiles with one hydrophilic end group, are inactive. These results are an exception to the rule-of-thumb that membrane-spanning bolaamphiphiles are inherently membrane-stabilizing molecules that inhibit all types of membrane transport.

  DOI：

  10.1021/ja0619253