N-[3,5-bis(tert-butyl)benzyl]cinchonidium bromide | 960161-13-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: N-[3,5-bis(tert-butyl)benzyl]cinchonidium bromide
• 英文别名: N-3,5-bis(tert-butylbenzyl)cinchonidinium bromide；(1S,2S,4S,5R)-1-(3,5-Di-tert-butylbenzyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide；(R)-[(1S,2S,4S,5R)-1-[(3,5-ditert-butylphenyl)methyl]-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;bromide
• CAS: 960161-13-1
• 化学式: Br*C₃₄H₄₅N₂O
• 分子量: 577.648
• InChiKey: HWRGTAJHVJCJHU-OOJJMGPJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,5-二叔丁基苄溴 、 辛可尼丁 在 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 N-[3,5-bis(tert-butyl)benzyl]cinchonidium bromide
  参考文献：
  名称：

  生物活性茚满：对潜在合成消炎药PH46A的对映选择性合成路线的概念研究。

  摘要：

  PH46A是单一对映异构体，是1,2-茚满二聚体家族的成员。它具有两个具有S，S构型的连续立体生成中心，其中一个是四级中心，已被开发为治疗炎症和自身免疫性疾病的临床候选药物。当前合成PH46A的途径涉及生成不需要的对映异构体（R，R）-7，从而显着降低最终收率。因此，我们研究了潜在的替代品，以提高这种合成的效率。该研究的第一阶段已经证明了使用相转移催化进行酮3的手性烷基化的原理证明，提供了关键的中间体酮（S）-4。还已经确定了合成PH46A，奎宁或辛可尼定所需的母体生物碱。迄今为止，对映体过量的可能性高达50％，使用替代底物不饱和酮9也为进一步的研究开辟了进一步的途径。研究的第二部分涉及初步筛选一组水解酶对（rac）-4的作用，以鉴定潜在的化学酶促途径，以优化在合成早期将手性引入PH46A中。水解酶模块也产生了积极的结果。具有MtBE的AH-46酶可提供8.4的选择性因子，对映体过量为77

  DOI：

  10.3390/molecules23071503

文献信息

• An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane
  作者：Maria Moccia、Robert J. Wells、Mauro. F. A. Adamo

  DOI：10.1039/c4ob02109f

  日期：——

  Herein, we describe a short synthesis of 3-methyl-4-nitro-5-alkylethenyl isoxazoles and their reactivity as Michael acceptors. The title compounds reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee) which were then converted to the corresponding γ-nitroacids.

  在这里，我们描述了3-甲基-4-硝基-5-烷基乙烯基异恶唑的简短合成及其作为迈克尔受体的反应性。在相转移催化下，标题化合物与硝基甲烷反应，得到高度对映体富集的加合物（最高93％ee），然后将其转化为相应的γ-硝酸。
• Synthesis of green organogelators with a sulfide linkage via solvent-free Michael addition: soft templates for the preparation of size-controlled gold nanoparticles
  作者：Frederic Delbecq、Katsura Tsujimoto、Yuki Ogue、Takeshi Kawai

  DOI：10.1016/j.tetlet.2012.11.145

  日期：2013.2

  Green organogelators with a sulfide linkage and free amino groups were synthesized via phase transfer catalysis using a N-benzylcinchonidinium bromide catalyst. Their self-assemblies in various common solvents were examined. These compounds exhibit high gelation ability especially in aromatic and highly polar solvents with a low critical gelation of 0.1 wt %. The organogels were analyzed by H-1 nuclear magnetic resonance (H-1 NMR) and Fourier transfer-infrared spectroscopies (FT-IR), and their phase transition temperatures were determined by differential scanning calorimetry. The homogeneity of the gel networks was examined by field emission scanning electron microscopy and transmission electron microscopy (TEM). A lamellar structure was also confirmed by X-ray diffraction analysis. The organogels were employed as soft-templates for the in situ generation of stable gold nanoparticles dispersed in the gel matrix, and the resulting GNP dispersions were studied by H-1 NMR and UV-vis absorption. Transmission electron microscopy showed that GNPs assemble into a thin membrane-like structure. (c) 2012 Elsevier Ltd. All rights reserved.