6-(2,5-二甲基-1H-吡咯-1-基)己烷-1-醇 | 280133-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 6-(2,5-二甲基-1H-吡咯-1-基)己烷-1-醇
• 英文名称: 6-(2,5-dimethylpyrrol-1-yl)hexan-1-ol
• 英文别名: 6-(2,5-dimethyl-1H-pyrrol-1-yl)hexan-1-ol
• CAS: 280133-18-8
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: WUWDKNYFFHTZLF-UHFFFAOYSA-N

物化性质

• 沸点：
  320.7±30.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(2,5-二甲基-1H-吡咯-1-基)己烷-1-醇 在 盐酸羟胺 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 6-[(6-aminohexyl)oxy]-2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Quantum Dot Based Luminescent Nanoprobes for Sigma-2 Receptor Imaging

  摘要：

  The increasing importance of sigma-2 receptor as target for the diagnosis and therapy of tumors paves the way for the development of innovative optically traceable fluorescent probes as tumor cell contrast and therapeutic agents. Here, a novel hybrid organic-inorganic nanostructure is developed by combining the superior fluorescent properties of inorganic quantum dots (QDs), coated with a hydrophilic silica shell (QD@SiO2 NPs), the versatility of the silica shell, and the high selectivity for sigma-2 receptor of the two synthetic ligands, namely, the 6-[(6-aminohexyl)oxy]-2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-Apropy1)-3,4-dihydroisoquinolin-1(2H)-one (MLP66) and 6-[1-[3-(4-cyclohexylpiperazin-1-yl)propyI]-1,2,3,4-tetrahydronaphtha- len-5-yloxylhexylamine (TA6). The proposed nanostructures represent a challenging alternative to all previously studied organic small fluorescent molecules, based on the same sigma-2 receptor affinity moieties. Flow cytometry and confocal fluorescence microscopy experiments, respectively, on fixed and living cancerous MCF7 cells, which overexpress the sigma-2 receptor, prove the ability of functionalized (QD@SiO2-TA(6) and QD@SiO2-MLP66) NPs to be internalized and demonstrate their affinity to the sigma-2 receptor, ultimately validating the targeting properties conveyed to the NPs by sigma-2 ligand conjugation. The presented QD-based nanoprobes possess a great potential as in vitro selective sigma-2 receptor imaging agent and, consequently, could provide a significant impact to future theranostic applications.

  DOI：

  10.1021/acs.molpharmaceut.7b00825
• 作为产物：
  描述：

  6-氨基-1-己醇 、 2,5-己二酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以82%的产率得到6-(2,5-二甲基-1H-吡咯-1-基)己烷-1-醇
  参考文献：
  名称：

  Quantum Dot Based Luminescent Nanoprobes for Sigma-2 Receptor Imaging

  摘要：

  The increasing importance of sigma-2 receptor as target for the diagnosis and therapy of tumors paves the way for the development of innovative optically traceable fluorescent probes as tumor cell contrast and therapeutic agents. Here, a novel hybrid organic-inorganic nanostructure is developed by combining the superior fluorescent properties of inorganic quantum dots (QDs), coated with a hydrophilic silica shell (QD@SiO2 NPs), the versatility of the silica shell, and the high selectivity for sigma-2 receptor of the two synthetic ligands, namely, the 6-[(6-aminohexyl)oxy]-2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-Apropy1)-3,4-dihydroisoquinolin-1(2H)-one (MLP66) and 6-[1-[3-(4-cyclohexylpiperazin-1-yl)propyI]-1,2,3,4-tetrahydronaphtha- len-5-yloxylhexylamine (TA6). The proposed nanostructures represent a challenging alternative to all previously studied organic small fluorescent molecules, based on the same sigma-2 receptor affinity moieties. Flow cytometry and confocal fluorescence microscopy experiments, respectively, on fixed and living cancerous MCF7 cells, which overexpress the sigma-2 receptor, prove the ability of functionalized (QD@SiO2-TA(6) and QD@SiO2-MLP66) NPs to be internalized and demonstrate their affinity to the sigma-2 receptor, ultimately validating the targeting properties conveyed to the NPs by sigma-2 ligand conjugation. The presented QD-based nanoprobes possess a great potential as in vitro selective sigma-2 receptor imaging agent and, consequently, could provide a significant impact to future theranostic applications.

  DOI：

  10.1021/acs.molpharmaceut.7b00825

文献信息

• 10.1021/jacs.4c05246
  作者：Strauss, Michael J.、Liu, Kaylee X.、Greaves, Megan E.、Dahl, Jakob C.、Kim, Seoung-Tae、Wu, Yong-Jin、Schmidt, Michael A.、Scola, Paul M.、Buchwald, Stephen L.

  DOI：10.1021/jacs.4c05246

  日期：——

  these reactions completely and exclusively promoted C–N coupling regardless of the structure of the amino alcohol. The ability to invert the observed chemoselectivity is distinct from previously described methods that require protecting group manipulations or rely entirely on steric effects to control reactivity. These results substantially improve the scope of Cu-catalyzed C–N coupling reactions using

  我们报告了一种通用的、官能团耐受的方法，用于铜催化碱敏感芳基溴化物的胺化，包括具有酸性官能团和小五元杂芳烃的底物。本文提出的结果大大扩展了铜催化的 C-N 偶联反应的范围。 L8 （阴离子N 1 , N 2 -二芳基苯-1,2-二胺配体）与弱碱 NaOTMS 的组合导致形成稳定但具有反应性的催化剂，该催化剂可防止因配位到杂环或带电中间体而失活。该系统能够使用低催化剂和配体负载。利用Cu· L8催化的C-O和C-N偶联反应中亲核体去质子化的差异，我们开发了一种化学选择性N-和O-芳基化多种氨基醇底物的方法。当氨基醇具有伯醇和更多受阻胺或苯胺基团时，使用 NaO t -Bu 作为碱只会导致 C-O 偶联。利用 NaOTMS 能够完全克服这些反应的空间选择性，并专门促进 C-N 偶联，无论氨基醇的结构如何。反转观察到的化学选择性的能力与之前描述的需要保护基团操作或完全依赖空间效应来控制反应性的方法不同。这些结果大大提高了使用N
• Quantum Dot Based Luminescent Nanoprobes for Sigma-2 Receptor Imaging
  作者：Maria Laura Pati、Elisabetta Fanizza、Sonja Hager、Diana Groza、Petra Heffeter、Amelita Grazia Laurenza、Valentino Laquintana、Maria Lucia Curri、Nicoletta Depalo、Carmen Abate、Nunzio Denora

  DOI：10.1021/acs.molpharmaceut.7b00825

  日期：2018.2.5

  The increasing importance of sigma-2 receptor as target for the diagnosis and therapy of tumors paves the way for the development of innovative optically traceable fluorescent probes as tumor cell contrast and therapeutic agents. Here, a novel hybrid organic-inorganic nanostructure is developed by combining the superior fluorescent properties of inorganic quantum dots (QDs), coated with a hydrophilic silica shell (QD@SiO2 NPs), the versatility of the silica shell, and the high selectivity for sigma-2 receptor of the two synthetic ligands, namely, the 6-[(6-aminohexyl)oxy]-2-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-Apropy1)-3,4-dihydroisoquinolin-1(2H)-one (MLP66) and 6-[1-[3-(4-cyclohexylpiperazin-1-yl)propyI]-1,2,3,4-tetrahydronaphtha- len-5-yloxylhexylamine (TA6). The proposed nanostructures represent a challenging alternative to all previously studied organic small fluorescent molecules, based on the same sigma-2 receptor affinity moieties. Flow cytometry and confocal fluorescence microscopy experiments, respectively, on fixed and living cancerous MCF7 cells, which overexpress the sigma-2 receptor, prove the ability of functionalized (QD@SiO2-TA(6) and QD@SiO2-MLP66) NPs to be internalized and demonstrate their affinity to the sigma-2 receptor, ultimately validating the targeting properties conveyed to the NPs by sigma-2 ligand conjugation. The presented QD-based nanoprobes possess a great potential as in vitro selective sigma-2 receptor imaging agent and, consequently, could provide a significant impact to future theranostic applications.