(4-(pyridin-2-yl)benzyl)morpholine | 1260901-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (4-(pyridin-2-yl)benzyl)morpholine
• 英文别名: 4-(4-(pyridin-2-yl)benzyl)morpholine；pbm；4-[(4-Pyridin-2-ylphenyl)methyl]morpholine；4-[(4-pyridin-2-ylphenyl)methyl]morpholine
• CAS: 1260901-19-6
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: AWFPBYVQFYBHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride 、 (4-(pyridin-2-yl)benzyl)morpholine 以 乙二醇乙醚 、 水 为溶剂， 反应 24.0h， 生成 Ir2Cl2((4-(pyridin-2-yl)benzyl)morpholine)4
  参考文献：
  名称：

  Biscylometalated iridium(iii) complexes target mitochondria or lysosomes by regulating the lipophilicity of the main ligands

  摘要：

  提出了一种有效的方法，控制双环金属铱(iii)配合物以靶向线粒体或溶酶体。

  DOI：

  10.1039/c6dt03328h
• 作为产物：
  描述：

  4-溴甲基苯硼酸频哪醇酯 在 四丁基溴化铵 、 palladium diacetate 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.84h， 生成 (4-(pyridin-2-yl)benzyl)morpholine
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g

文献信息

• Biscylometalated iridium(<scp>iii</scp>) complexes target mitochondria or lysosomes by regulating the lipophilicity of the main ligands
  作者：Kangqiang Qiu、Yukang Liu、Huaiyi Huang、Chaofeng Liu、Hongyi Zhu、Yu Chen、Liangnian Ji、Hui Chao

  DOI：10.1039/c6dt03328h

  日期：——

  An efficient method that controls biscylometalated iridium(iii) complexes to target mitochondria or lysosomes was presented.

  提出了一种有效的方法，控制双环金属铱(iii)配合物以靶向线粒体或溶酶体。
• Microwave-Mediated Synthesis of an Arylboronate Library
  作者：John Spencer、Christine B. Baltus、Hiren Patel、Neil J. Press、Samantha K. Callear、Louise Male、Simon J. Coles

  DOI：10.1021/co100011g

  日期：2011.1.10

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 11-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.
• Bimodal Visualization of Endogenous Nitric Oxide in Lysosomes with a Two-Photon Iridium(III) Phosphorescent Probe
  作者：Weijun Wu、Ruilin Guan、Xinxing Liao、Xu Yan、Thomas W. Rees、Liangnian Ji、Hui Chao

  DOI：10.1021/acs.analchem.9b02415

  日期：2019.8.6

  Nitric oxide (NO) is a fundamental signaling molecule that shows complex effects on the catabolic autophagy process, which is closely linked with lysosomal function. In this study, a new lysosome-targeted, pH-independent, and two-photon phosphorescent iridium(III) complex, Ir-BPDA, has been investigated for endogenous NO detection and imaging. The rational design of the probe, as the addition of the morpholine moieties and the substitution of a benzyl group in the amino group in Ir-BPDA, facilitates its accumulation in lysosomes and makes the reaction product with NO, Ir-BPDA-NO, insusceptible in its phosphorescence intensity and lifetime against pH changes (pH 4–10), well suited for lysosomal NO detection (pH 4–6). Furthermore, Ir-BPDA exhibits a fast and 50-fold response to NO in phosphorescence intensity and a two-photon cross-section as high as 60 GM after the reaction, as well as a notably increased phosphorescence lifetime from 200.1 to 619.6 ns. Thus, accompanied by its photostability, Ir-BPDA enabled the detection of NO in the lipopolysaccharide-stimulated macrophages and zebrafish model, revealing the endogenous lysosomal NO distribution during inflammation in vivo by means of both TPM and PLIM imaging techniques.

  一氧化氮（NO）是一种基本的信号分子，对分解性自噬过程产生复杂影响，该过程与溶酶体功能密切相关。本研究中，探讨了一种新的靶向溶酶体、pH独立的双光子磷光铱(III)复合物Ir-BPDA，用于内源性NO的检测和成像。该探针的合理设计，尤其是在Ir-BPDA中添加了吗啉基并替换了氨基中的苄基，有助于其在溶酶体中的积累，使与NO反应生成的产物Ir-BPDA-NO在磷光强度和寿命上对pH变化（pH 4-10）不敏感，适合用于溶酶体的NO检测（pH 4-6）。此外，Ir-BPDA在与NO反应后表现出快速且高达50倍的磷光强度响应，并且双光子相互作用截面高达60 GM，相应的磷光寿命显著增加，从200.1 ns增加至619.6 ns。因此，结合其光稳定性，Ir-BPDA能够在脂多糖刺激的巨噬细胞和斑马鱼模型中检测NO，通过双光子显微术（TPM）和相位荧光成像（PLIM）技术揭示了体内炎症过程中内源性溶酶体NO的分布。