(3R)-3-乙烯基-1-氮杂双环[2.2.2]辛烷 | 1311205-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 中文名称: (3R)-3-乙烯基-1-氮杂双环[2.2.2]辛烷
• 英文名称: (3R)-3-ethenyl-1-azabicyclo[2.2.2]octane
• 英文别名: 3-vinyl-1-azabicyclo[2.2.2]octane
• CAS: 1311205-56-7
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: STMXRYQUMAMCAF-QMMMGPOBSA-N

物化性质

• 沸点：
  174.2±19.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3R)-3-乙烯基-1-氮杂双环[2.2.2]辛烷 在 吡啶 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 氯仿 为溶剂， 反应 22.75h， 生成 10-(1-氮杂双环[2.2.2]辛-3-基甲基)-10H-吩噻嗪
  参考文献：
  名称：

  VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE

  摘要：

  本发明涉及使用以下式子2的乙烯喹诺啉（R）对映体作为合成(R)-美奎嗪的中间体。

  公开号：

  US20130296553A1
• 作为产物：
  描述：

  (3R,4S)-4-(2-氯乙基)-3-乙烯基哌啶 以75的产率得到(3R)-3-乙烯基-1-氮杂双环[2.2.2]辛烷
  参考文献：
  名称：

  VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE

  摘要：

  本发明涉及使用下式2的乙烯基喹硫吡啶对映体（R）作为(R)-美曲嗪的合成中间体。

  公开号：

  US20130296553A1

文献信息

• Asymmetric Synthesis of (+)-Mequitazine from Quinine
  作者：Sébastien Leroux、Laurent Larquetoux、Marc Nicolas、Eric Doris

  DOI：10.1021/ol2012567

  日期：2011.7.1

  The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.
• Lukes; Galik, Collection of Czechoslovak Chemical Communications, 1953, vol. 18, p. 829,831
  作者：Lukes、Galik

  DOI：——

  日期：——
• Ambient UVA-Induced Expression of p53 and Apoptosis in Human Skin Melanoma A375 Cell Line by Quinine
  作者：Neera Yadav、Ashish Dwivedi、Syed Faiz Mujtaba、Hari Narayan Kushwaha、Shio Kumar Singh、Ratan Singh Ray

  DOI：10.1111/php.12047

  日期：2013.5

  AbstractThis study aimed to analyze the phototoxic mechanism and photostability of quinine in human skin cell line A375 under ambient intensities of UVA (320–400 nm). Photosensitized quinine produced a photoproduct 6‐methoxy‐quinoline‐4‐ylmethyl‐oxonium identified through LC‐MS/MS. Generation of 1O2, O2•−, and •OH was measured and further substantiated through their respective quenchers. Photosensitized Quinine (Q) caused degradation of 2‐deoxyguanosine, the most sensitive nucleotide to UV radiation. The intracellular ROS was increased in a concentration‐dependent manner. Significant reduction in metabolic status measured in terms of cell viability (54%) at 25 μg mL−1 was observed through MTT assay. Results of MTT assay accord NRU assay. Single strand DNA breaks and apoptosis were increased significantly (P < 0.01) as observed through comet assay and EB/AO double staining. Photosensitized quinine caused cells to arrest in G2 phase of cell cycle and induced apoptosis (5.08%) as revealed through FACS. Real‐Time PCR showed upregulation of p21 (4.56 folds) and p53 (2.811 folds) genes expression. Thus, our study suggests that generation of reactive oxygen species by quinine under ambient intensity of UVA may result into deleterious phototoxic effects among human population.
• Org. Lett. 2011, 13, 3549-3551
  作者：

  DOI：——

  日期：——
• VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE
  申请人：Nicolas Marc

  公开号：US20130296553A1

  公开（公告）日：2013-11-07

  The present invention relates to the use of the vinyl quinuclidine enantiomer (R) of the following formula 2 as a synthesis intermediate in the preparation of (R)-mequitazine.

  本发明涉及使用以下式子2的乙烯喹诺啉（R）对映体作为合成(R)-美奎嗪的中间体。