N-[3,5-bis(trifluoromethyl)benzyl]cinchonidium bromide | 947508-16-9

• 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(trifluoromethyl)benzyl]cinchonidium bromide
• 英文别名: (9R)-1-[3,5-Bis(trifluoromethyl)benzyl]cinchonan-1-ium-9-ol bromide；(1S,2S,4S,5R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(quinolin-4-yI)methyl)-5-vinylquinuclidin-1-ium bromide；(1S,2S,4S,5R)-1-(3,5-Bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide；(R)-[(1S,2S,4S,5R)-1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;bromide
• CAS: 947508-16-9
• 化学式: Br*C₂₈H₂₇F₆N₂O
• 分子量: 601.43
• InChiKey: CLNARDUAXMLYOH-NNFVHLLNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苄基溴 、 辛可尼丁 以 四氢呋喃 为溶剂， 以88%的产率得到N-[3,5-bis(trifluoromethyl)benzyl]cinchonidium bromide
  参考文献：
  名称：

  对映选择性相转移催化的1-甲基-7-甲氧基-2-四氢萘酮的烷基化：脱佐辛的有效途径。

  摘要：

  为了不对称地制备（R）-（+）-1-（5-溴戊基）-1-甲基-7-甲氧基-2-四氢萘酮（3a），制备了地佐辛的关键中间体17金鸡纳生物碱衍生催化剂并用1，5-二溴戊烷筛选1-甲基-7-甲氧基-2-四氢萘酮的对映选择性烷基化反应，并确定了最佳催化剂（C7）。另外，对烷基化进行了优化，使得该方法变得实用和有效。

  DOI：

  10.3762/bjoc.14.119
• 作为试剂：
  描述：

  正辛醛 在 N-[3,5-bis(trifluoromethyl)benzyl]cinchonidium bromide 、 potassium carbonate 、 甲基磺酰氯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 111.0h， 生成 (S)-3-methyl-4-nitro-5-(2-(nitromethyl)nonyl)isoxazole 、 (R)-3-methyl-4-nitro-5-(2-(nitromethyl)nonyl)isoxazole
  参考文献：
  名称：

  制备3-甲基-4-硝基亚烷基乙基异恶唑的改进方法及其在硝基甲烷催化对映选择性迈克尔加成反应中的反应†

  摘要：

  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。

  DOI：

  10.1039/c4ob02109f

文献信息

• Piperidinone carboxamide indane CGRP receptor antagonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US09499541B2

  公开（公告）日：2016-11-22

  The present invention is directed to piperidinone carboxamide indane derivatives which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which the CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

  本发明涉及哌啶酮羧酰胺茚烷衍生物，其为CGRP受体拮抗剂，可用于治疗或预防CGRP参与的疾病，如偏头痛。该发明还涉及包含这些化合物的药物组合物，以及在预防或治疗CGRP参与的这类疾病中使用这些化合物和组合物。
• Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts
  作者：Weihua Li、Yifeng Wang、Danqian Xu

  DOI：10.1039/c8ob02484g

  日期：——

  A highly enantioselective nucleophilic addition of ketones to imines catalyzed by chiral phase-transfer catalysts (N-quaternised cinchona alkaloid ammonium salts) has been developed, and the process affords the Mannich reaction products with tertiary stereocenters in good to high yields (up to 95%) with excellent enantioselectivities (up to 97% ee).

  已开发出手性相转移催化剂（N-季铵化金鸡纳生物碱铵盐）催化的亚胺向酮的高度对映选择性亲核加成反应，该方法可提供具有高到高收率（高达95％）的叔立体中心的曼尼希反应产物。 ）具有出色的对映选择性（ee高达97％）。
• WO2018211275A5
  申请人：——

  公开号：WO2018211275A5

  公开（公告）日：2022-11-22
• 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.
• 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。