N,N'-di(naphthoyl)-L-cystine diamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-di(naphthoyl)-L-cystine diamide
• 英文别名: naphth-2-oyl-Cys(1)-NH2.naphth-2-oyl-Cys(1)-NH2；N-[(2R)-1-amino-3-[[(2R)-3-amino-2-(naphthalene-2-carbonylamino)-3-oxopropyl]disulfanyl]-1-oxopropan-2-yl]naphthalene-2-carboxamide
• 化学式: C₂₈H₂₆N₄O₄S₂
• 分子量: 546.671
• InChiKey: QYTUZUKPQPEKOS-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-di(naphthoyl)-L-cystine diamide 在 1,4-dithio-D,L-threitol 、 对甲苯磺酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 72.5h， 生成 methyl (2-naphthoyl)-L-cysteinate
  参考文献：
  名称：

  Detecting a peroxide-based explosive via molecular gelation

  摘要：

  利用硫醇到二硫化物的氧化反应触发溶液到凝胶的相变，开发出了一种方便携带的三丙酮三过氧化物（TATP）传感器。使用这种方法，无需任何仪器即可直观地检测 TATP。

  DOI：

  10.1039/c2cc33486k
• 作为产物：
  描述：

  N-[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]naphthalene-2-carboxamide 在 甘油三酸酯过氧化物 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.13h， 生成 N,N'-di(naphthoyl)-L-cystine diamide
  参考文献：
  名称：

  Detecting a peroxide-based explosive via molecular gelation

  摘要：

  利用硫醇到二硫化物的氧化反应触发溶液到凝胶的相变，开发出了一种方便携带的三丙酮三过氧化物（TATP）传感器。使用这种方法，无需任何仪器即可直观地检测 TATP。

  DOI：

  10.1039/c2cc33486k

文献信息

• Anatomy of a Gel. Amino Acid Derivatives That Rigidify Water at Submillimolar Concentrations
  作者：Fredric M. Menger、Kevin L. Caran

  DOI：10.1021/ja0016811

  日期：2000.11.1

  On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating, ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that pi/pi stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 degreesC. Other gels have a "catastrophic" break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this "anatomy" of a gel.
• Detecting a peroxide-based explosive via molecular gelation
  作者：Jing Chen、Weiwei Wu、Anne J. McNeil

  DOI：10.1039/c2cc33486k

  日期：——

  A convenient and portable triacetone triperoxide (TATP) sensor was developed utilizing a thiol-to-disulfide oxidation to trigger a solution-to-gel phase transition. Using this method, TATP can be detected visually without any instrumentation.

  利用硫醇到二硫化物的氧化反应触发溶液到凝胶的相变，开发出了一种方便携带的三丙酮三过氧化物（TATP）传感器。使用这种方法，无需任何仪器即可直观地检测 TATP。