1-bromo-6-oxadodecane | 157194-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-6-oxadodecane
• 英文别名: 1-(5-Bromopentoxy)hexane
• CAS: 157194-15-5
• 化学式: C₁₁H₂₃BrO
• 分子量: 251.207
• InChiKey: CXEOTKRFHXOQLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-6-oxadodecane 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly

  摘要：

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.

  DOI：

  10.1021/ja00092a008
• 作为产物：
  描述：

  1,5-二溴戊烷 、 正己醇 在 sodium 作用下， 生成 1-bromo-6-oxadodecane
  参考文献：
  名称：

  Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly

  摘要：

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.

  DOI：

  10.1021/ja00092a008

文献信息

• A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase
  作者：Daniël Lahav、Bing Liu、Richard J. B. H. N. van den Berg、Adrianus M. C. H. van den Nieuwendijk、Tom Wennekes、Amar T. Ghisaidoobe、Imogen Breen、Maria J. Ferraz、Chi-Lin Kuo、Liang Wu、Paul P. Geurink、Huib Ovaa、Gijsbert A. van der Marel、Mario van der Stelt、Rolf G. Boot、Gideon J. Davies、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1021/jacs.7b07352

  日期：2017.10.11

  assessed on GBA2 selectivity offset against the other glucosylceramide metabolizing enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA), and the cytosolic retaining β-glucosidase, GBA3. Our work, yielding potent and selective GBA2 inhibitors, also provides a roadmap for the development of high-throughput assays for identifying retaining glycosidase inhibitors by FluoPol-ABPP

  人非溶酶体葡萄糖基神经酰胺酶（GBA2）是控制糖脂水平的几种酶之一，其活性与几种人类疾病状态相关。迫切需要设计或发现选择性的GBA2抑制剂作为化学工具和潜在的治疗剂。在这里，我们描述了基于荧光偏振活性的蛋白质谱分析（FluoPol-ABPP）测定法的发展，该测定法可从350多种亚氨基糖文库中快速鉴定GBA2抑制剂。基于FluoPol-ABPP筛选的线索生成聚焦库，并针对与其他葡糖神经酰胺代谢酶，葡糖神经酰胺合酶（GCS），溶酶体葡糖神经酰胺酶（GBA）和胞质保留β-葡糖苷酶GBA3的GBA2选择性偏移进行评估。我们的工作产生了有效的和选择性的GBA2抑制剂，
• Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly
  作者：Yuichi Ishikawa、Hiroaki Kuwahara、Toyoki Kunitake

  DOI：10.1021/ja00092a008

  日期：1994.6

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.