{(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine | 438226-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine
• 英文别名: N-[[5,5-bis(dodecoxymethyl)-1,3-dithian-2-yl]-[4-(oxan-2-yloxy)phenyl]methyl]-5-nitropyridin-2-amine
• CAS: 438226-87-0
• 化学式: C₄₇H₇₇N₃O₆S₂
• 分子量: 844.277
• InChiKey: OIKNMGAJCFDIQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  58
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以73.3%的产率得到4-[(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-(5-nitro-pyridin-2-ylamino)-methyl]-phenol
  参考文献：
  名称：

  Liposomes from Novel Photolabile Phospholipids:  Light-Induced Unloading of Small Molecules As Monitored by PFG NMR

  摘要：

  A molecular dithiane-based approach to synthesis of novel photolabile phospholipids is developed. These lipids are used in formulations with egg-POPC and cholesterol to prepare light-sensitive liposomes. Irradiation of such liposomes in PBS buffer (medium pressure mercury lamp, Pyrex filter, lambda > 300 nm) significantly increases the bilayer permeability and accelerates the release of entrapped small organic molecules by an order of magnitude. A simple assay, based on (1)H or (19)F PFG NMR measurements of diffusion coefficients, is developed to monitor light-induced unloading of the probe molecules.

  DOI：

  10.1021/ja016874i
• 作为产物：
  描述：

  (5-hydroxymethyl-[1,3]dithian-5-yl)-methanol 在 正丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 20.0h， 生成 {(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine
  参考文献：
  名称：

  Liposomes from Novel Photolabile Phospholipids:  Light-Induced Unloading of Small Molecules As Monitored by PFG NMR

  摘要：

  A molecular dithiane-based approach to synthesis of novel photolabile phospholipids is developed. These lipids are used in formulations with egg-POPC and cholesterol to prepare light-sensitive liposomes. Irradiation of such liposomes in PBS buffer (medium pressure mercury lamp, Pyrex filter, lambda > 300 nm) significantly increases the bilayer permeability and accelerates the release of entrapped small organic molecules by an order of magnitude. A simple assay, based on (1)H or (19)F PFG NMR measurements of diffusion coefficients, is developed to monitor light-induced unloading of the probe molecules.

  DOI：

  10.1021/ja016874i

文献信息

• Liposomes from Novel Photolabile Phospholipids:  Light-Induced Unloading of Small Molecules As Monitored by PFG NMR
  作者：Yongqin Wan、Joseph K. Angleson、Andrei G. Kutateladze

  DOI：10.1021/ja016874i

  日期：2002.5.1

  A molecular dithiane-based approach to synthesis of novel photolabile phospholipids is developed. These lipids are used in formulations with egg-POPC and cholesterol to prepare light-sensitive liposomes. Irradiation of such liposomes in PBS buffer (medium pressure mercury lamp, Pyrex filter, lambda > 300 nm) significantly increases the bilayer permeability and accelerates the release of entrapped small organic molecules by an order of magnitude. A simple assay, based on (1)H or (19)F PFG NMR measurements of diffusion coefficients, is developed to monitor light-induced unloading of the probe molecules.