N,N'-bis(N-benzyloxycarbonyl)-1,24-diamino-4,21-dioxa-5,20-dioxotetracosane | 217471-34-6

• 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: N,N'-bis(N-benzyloxycarbonyl)-1,24-diamino-4,21-dioxa-5,20-dioxotetracosane
• CAS: 217471-34-6
• 化学式: C₃₈H₅₆N₂O₈
• 分子量: 668.871
• InChiKey: WITCBJNFNDECQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  48.0
• 可旋转键数：
  27.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(N-benzyloxycarbonyl)-1,24-diamino-4,21-dioxa-5,20-dioxotetracosane 在 Pd(C 吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 N,N'-bis(1R,2R-3,6,9,12,15,18-hexaoxacycloocta-2-carboxyl-1-carbonyl)-1,24-diamino-4,21-dioxa-5,20-dioxotetracosane
  参考文献：
  名称：

  Chemical Switching of Vesicle Bilayer Membrane Disruption by Bis(crown ether) Bolaamphiphiles

  摘要：

  Bis(crown ether) bolaamphiphiles derived from 18-crown-6 dicarboxylic acid were prepared, and their ability to release vesicle encapsulated 5[6]-carboxyfluorescein was determined. Bolaamphiphiles with a linear central spacer are poor membrane disrupting agents except in the presence of alkaline earth metal cations or ethylenediammonium cation. Divalent ion enhancement of membrane disruption is cation selective and can be used to determine the apparent association constant of the bolaamphiphile crown ether with the added cation. The cis-isomer of a thioindigo bis(crown ether) bolaamphiphile is an active membrane disrupting agent, but the trans-isomer is significantly less active. In homogeneous solution, cis-to-trans thermal and photochemical isomerization is retarded by added alkaline earth metal salts, indicating that cooperative ditopic binding of the cations occurs despite the inherent flexibility of the bolaamphiphile. The membrane disruption mechanism occurs via U-shaped conformations of the bolaamphiphile. All available data indicate that divalent cations accelerate membrane disruption by stabilization of the U-shaped conformation via cooperative interaction of the crown ethers with the dication. Thus the membrane disruption process is switched "on" by molecular recognition.

  DOI：

  10.1021/jo981195k
• 作为产物：
  描述：

  十六碳二酸 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 N,N'-bis(N-benzyloxycarbonyl)-1,24-diamino-4,21-dioxa-5,20-dioxotetracosane
  参考文献：
  名称：

  Chemical Switching of Vesicle Bilayer Membrane Disruption by Bis(crown ether) Bolaamphiphiles

  摘要：

  Bis(crown ether) bolaamphiphiles derived from 18-crown-6 dicarboxylic acid were prepared, and their ability to release vesicle encapsulated 5[6]-carboxyfluorescein was determined. Bolaamphiphiles with a linear central spacer are poor membrane disrupting agents except in the presence of alkaline earth metal cations or ethylenediammonium cation. Divalent ion enhancement of membrane disruption is cation selective and can be used to determine the apparent association constant of the bolaamphiphile crown ether with the added cation. The cis-isomer of a thioindigo bis(crown ether) bolaamphiphile is an active membrane disrupting agent, but the trans-isomer is significantly less active. In homogeneous solution, cis-to-trans thermal and photochemical isomerization is retarded by added alkaline earth metal salts, indicating that cooperative ditopic binding of the cations occurs despite the inherent flexibility of the bolaamphiphile. The membrane disruption mechanism occurs via U-shaped conformations of the bolaamphiphile. All available data indicate that divalent cations accelerate membrane disruption by stabilization of the U-shaped conformation via cooperative interaction of the crown ethers with the dication. Thus the membrane disruption process is switched "on" by molecular recognition.

  DOI：

  10.1021/jo981195k