N¹-3-bromopropanoyl-N²,N³-didodecyl-L-glutamide | 131211-22-8

• 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: N¹-3-bromopropanoyl-N²,N³-didodecyl-L-glutamide
• 英文别名: N,N'-didodecyl-N^α-3-bromopropanoyl-L-glutamide
• CAS: 131211-22-8
• 化学式: C₃₂H₆₂BrN₃O₃
• 分子量: 616.767
• InChiKey: JSSGIJBCRCTODA-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  39.0
• 可旋转键数：
  29.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  87.3
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N¹-3-bromopropanoyl-N²,N³-didodecyl-L-glutamide 、 N-甲基-4,4'-联吡啶鎓碘化物 以 乙腈 为溶剂， 反应 50.0h， 以29%的产率得到
  参考文献：
  名称：

  化学氧化还原诱导的紫精超分子组装体的手性光学转换

  摘要：

  使用紫精修饰的谷酰胺（ G -V 2+ ）衍生物制备了手性超分子组装体，其手性光学性质表现出氧化还原诱导的变化。 G -V 2+组装中的非手性紫精部分通过谷氨酰胺基团进行手性取向，提供独特的橙色溶液，在 470 nm 左右具有可见吸收带，具有电子圆二色性 (CD) 信号（摩尔椭圆率 [ θ ] = 0.58 × 10 5 deg cm 2 dmol -1 : 吸收不对称因子 ( g ) = 5.2 × 10 -3 (512 nm)。 G -V 2+可以还原为其阳离子基团（ G -V + ˙），但保留其手性组装。化学还原后，颜色从橙色变为蓝紫色，表明在约560 nm处有吸收带，CD信号的符号从正变为负（[ θ ] = -0.36 × 10 5 deg cm 2 dmol -1 ; g = -2.9 × 10 -3 (580 nm) 在水中观察到。随后的氧化重新引入还原前的G -V 2+手性光学行为。

  DOI：

  10.1039/d1ra08984f
• 作为产物：
  描述：

  3-溴丙酸 、 在 氰基磷酸二乙酯 、 三乙胺 作用下， 生成 N¹-3-bromopropanoyl-N²,N³-didodecyl-L-glutamide
  参考文献：
  名称：

  Amphiphilic molecular gels from ω-aminoalkylated l-glutamic acid derivatives with unique chiroptical properties

  摘要：

  Self-assembling amphiphiles with unique chiroptical properties were derived from l-glutamic acid through omega-aminoalkylation and double long-chain alkylation. These amphiphiles can disperse in various solvents ranging from water to n-hexane. TEM and SEM observations indicate that the improvement in dispersity is induced by the formation of tubular and/or fibrillar aggregates with nanosized diameters, which makes these amphiphiles similar to aqueous lipid membrane systems. Spectroscopic observations, such as UV-visible and CD spectroscopies indicate that the aggregates are constructed on the basis of S- and R-chirally ordered structures through interamide interactions in water and organic media, respectively, and that these chiroptical properties can be controlled thermotropically and lyotropically. It is also reported that the chiral assemblies provide specific binding sites for achiral molecules and then induce chirality for the bonded molecules. Further, the applicability of the amphiphiles to template polymerization is discussed.

  DOI：

  10.1007/s00726-010-0480-z

文献信息

• Enhanced Fluorescence of Loosely Packed Dye Aggregates
  作者：Naoya Ryu、Hiroshi Hachisako

  DOI：10.1246/cl.140962

  日期：2015.2.5

  The fluorescence of a hemicyanine dye was considerably enhanced by the formation of loosely packed aggregates, compared to tightly aggregated and molecularly dispersed hemicyanine dyes. Loose dye aggregates were realized by introducing a self-assembling unit to the dye molecules and by adjusting the mixture of good solvent and nonsolvent for the dye moiety.

  与紧密聚集和分子分散的半氰胺染料相比，松散聚集体的形成大大增强了半氰胺染料的荧光。通过在染料分子中引入自组装单元以及调整染料分子的良好溶剂和非溶剂混合物，可以实现松散的染料聚集。
• Induction of Strong and Tunable Circularly Polarized Luminescence of Nonchiral, Nonmetal, Low-Molecular-Weight Fluorophores Using Chiral Nanotemplates
  作者：Taisei Goto、Yutaka Okazaki、Masahiro Ueki、Yutaka Kuwahara、Makoto Takafuji、Reiko Oda、Hirotaka Ihara

  DOI：10.1002/anie.201612331

  日期：2017.3.6

  described for generating strong circularly polarized luminescence with highly tunable emission bands through chiral induction in nonchiral, totally organic, low‐molecular‐weight fluorescent dyes by chiral nanotemplate systems. Our approach allows the first systematic investigation to clarify the correlation between the circular dichroism and circularly polarized luminescence intensities. As a result, a

  描述了一种新的策略，通过手性纳米模板系统在非手性，完全有机，低分子量的荧光染料中进行手性诱导，可产生具有高度可调发射带的强圆偏振发光。我们的方法允许进行首次系统研究，以弄清圆二色性和圆偏振发光强度之间的相关性。结果，鉴定出迄今为止具有最高圆偏振发光强度并且不对称系数超过0.1的稀溶液系统。