(R,R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dicarboxylic acid anhydride | 76871-58-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R,R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dicarboxylic acid anhydride
• 英文别名: monoanhydride <18>-crown-6-R,R-tartaric acid；monoanhydride [18]-crown-6-R,R-tartaric acid；(1R,18R)-2,5,8,11,14,17,20-heptaoxabicyclo[16.3.0]henicosane-19,21-dione
• CAS: 76871-58-4
• 化学式: C₁₄H₂₂O₉
• 分子量: 334.323
• InChiKey: ZQOHVACKDYSJST-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R,R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dicarboxylic acid anhydride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到(1S,18R)-(+)-2,5,8,11,14,17,20-heptaoxabicyclo<16.3.0>heneicosan-19-one
  参考文献：
  名称：

  Synthesis of a Series of Functionalized Bis-Crown Ethers

  摘要：

  合成了一系列新的双环醚，具有酸、醇和胺侧链，以及酰亚胺和内酰胺功能。

  DOI：

  10.1055/s-1991-26483
• 作为产物：
  描述：

  R,R-(+)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3-dicarboxylic acid 在 乙酰氯 作用下， 生成 (R,R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dicarboxylic acid anhydride
  参考文献：
  名称：

  Synthesis of a Series of Functionalized Bis-Crown Ethers

  摘要：

  合成了一系列新的双环醚，具有酸、醇和胺侧链，以及酰亚胺和内酰胺功能。

  DOI：

  10.1055/s-1991-26483

文献信息

• Membrane transport. A proton-driven potassium ion pump
  作者：Laurel A. Frederick、Thomas M. Fyles、Virginia A. Malik-Diemer、Dennis M. Whitfield

  DOI：10.1039/c39800001211

  日期：——

  The functionalized crown ethers (1)–(3) act as carriers for the membrane transport of potassium ions against their concentration gradient by the coupled counter-transport of protons.

  功能化的冠醚（1）-（3）通过耦合的质子反转运，作为钾离子通过其浓度梯度膜运输的载体。
• Molecular recognition-controlled membrane disruption by a bis(crown ether) bola-amphiphile
  作者：Thomas M. Fyles、Binqi Zeng

  DOI：10.1039/cc9960002295

  日期：——

  Release of liposome-entrapped carboxyfluorescein is switched ‘on’via molecular recognition of barium ion by a bis(crown ether carboxylate) bola-amphiphile.

  通过双冠醚羧酸盐的球状两亲分子对钡离子的分子识别，释放包埋在脂质体中的氨基荧光素被“开启”。
• Photoionophores derived from crown ether polycarboxylic acids: synthesis, ion binding, and spectroscopic characterization
  作者：Thomas M. Fyles、Valia Veettil Suresh

  DOI：10.1139/v94-158

  日期：1994.5.1

  types of potential photoionophores based on polycarboxylic acid crown ethers were prepared, and their cation complexation behaviours and spectroscopic properties were surveyed. The first type were neutral macropolycyclic hosts prepared by capping across the faces of the crown ether with aromatic diamine chromophores. The second were bis-crown ether carboxylates bearing a bridging aromatic chromophore. The

  制备了三种基于聚羧酸冠醚的潜在光离子载体，并考察了它们的阳离子络合行为和光谱性能。第一种类型是中性大多环主体，通过用芳香二胺发色团覆盖冠醚表面制备。第二种是带有桥连芳香发色团的双冠醚羧酸盐。第三种类型在冠醚羧酸骨架上附加了一个额外的发色团供体位点。通过电位滴定检查阳离子络合。中性配体对于碱金属阳离子来说是相当差的宿主。另外两种类型的冠醚羧酸盐表现出尺寸选择性和静电稳定性的结合，导致水中显着的选择性离子结合。第三类配体在中性和碱性水溶液中也表现出依赖于阳离子的吸收光谱。没有明显的碱金属或碱土金属阳离子引起的扰动...
• Frederick, Laurel A.; Fyles, Thomas M.; Gurprasad, Narine P., Canadian Journal of Chemistry, 1981, vol. 59, p. 1724 - 1733
  作者：Frederick, Laurel A.、Fyles, Thomas M.、Gurprasad, Narine P.、Whitfield, Dennis M.

  DOI：——

  日期：——
• Chemical Switching of Vesicle Bilayer Membrane Disruption by Bis(crown ether) Bolaamphiphiles
  作者：T. M. Fyles、B. Zeng

  DOI：10.1021/jo981195k

  日期：1998.11.1

  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.