2-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride | 108716-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride
• 英文别名: 2-Phenyl-1,2,3,4-tetrahydroquinoline hydrochloride；2-phenyl-1,2,3,4-tetrahydroquinoline;hydrochloride
• CAS: 108716-07-0
• 化学式: C₁₅H₁₅N*ClH
• mdl: MFCD22369840
• 分子量: 245.752
• InChiKey: HSHKFRIVZVHEEG-UHFFFAOYSA-N

物化性质

• 熔点：
  229 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  16.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氰胺 、 2-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride 以 乙醇 为溶剂， 反应 48.0h， 以30%的产率得到1-carboximidamido-2-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride
  参考文献：
  名称：

  碳酸盐存在下钌催化的邻氨基苄醇与酮的无受体脱氢偶联至喹啉

  摘要：

  设计，合成了带有功能性2,2'-联苯并咪唑配体[（p- Cymene）Ru（BiBzImH 2）Cl] [Cl]的钌配合物，它是通过无受体合成喹啉的通用高效催化剂。碳酸盐存在下邻氨基苄醇与酮的脱氢偶联。证实了配体中的NH单元对于催化活性至关重要。还进行了该催化体系在生物活性分子的规模克合成中的应用。值得注意的是，这项研究展示了金属-配体双功能催化剂在无受体脱氢反应中的新潜力。

  DOI：

  10.1016/j.jcat.2020.12.016
• 作为产物：
  描述：

  2-苯基喹啉 在 盐酸 、 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以71%的产率得到2-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride
  参考文献：
  名称：

  碳酸盐存在下钌催化的邻氨基苄醇与酮的无受体脱氢偶联至喹啉

  摘要：

  设计，合成了带有功能性2,2'-联苯并咪唑配体[（p- Cymene）Ru（BiBzImH 2）Cl] [Cl]的钌配合物，它是通过无受体合成喹啉的通用高效催化剂。碳酸盐存在下邻氨基苄醇与酮的脱氢偶联。证实了配体中的NH单元对于催化活性至关重要。还进行了该催化体系在生物活性分子的规模克合成中的应用。值得注意的是，这项研究展示了金属-配体双功能催化剂在无受体脱氢反应中的新潜力。

  DOI：

  10.1016/j.jcat.2020.12.016

文献信息

• Design, Synthesis, and Pharmacological Evaluation of Conformationally Constrained Analogues of <i>N</i>,<i>N</i>‘-Diaryl- and <i>N</i>-Aryl-<i>N</i>-aralkylguanidines as Potent Inhibitors of Neuronal Na⁺ Channels
  作者：Michel C. Maillard、Michael E. Perlman、Oved Amitay、Deborah Baxter、David Berlove、Sonia Connaughton、James B. Fischer、Jun Qing Guo、Lain-Yen Hu、Robert N. McBurney、Peter I. Nagy、Katragadda Subbarao、Elizabeth A. Yost、Lu Zhang、Graham J. Durant

  DOI：10.1021/jm980124a

  日期：1998.7.1

  In the present investigation, the rationale for the design, synthesis, and biological evaluation of potent inhibitors of neuronal Nai channels is described. N,N'-Diaryl- and N-aryl-N-aralkylguanidine templates were locked in conformations mimicking the permissible conformations of the flexible diarylguanidinium ion (AS(+), AA(+), SS+). The resulting set of constrained guanidines termed "lockamers" (cyclophane, quinazoline, aminopyrimidazolines, aminoimidazolines azocino- and tetrahydroquinolinocarboximidamides) was examined for neuronal Na+ channel blockade properties. Inhibition of [C-14]guanidinium ion influx in CHO cells expressing type IIA Na+ channels showed that the aminopyrimidazoline 9b and aminoimidazoline 9d, compounds proposed to lock the N,N'-diarylguanidinium in an SS+ conformation, were the most potent Na+ channel blockers with IC50's of 0.06 mu M, a value 17 times lower than that of the parent flexible compound 18d. The rest of the restricted analogues with 4-p-alkyl substituents retained potency with IC50 values ranging between 0.46 and 2.9 mu M. Evaluation in a synaptosomal Ca-45(2+) influx assay showed that 9b did not exhibit high selectivity for neuronal Na+ vs Ca2+ channels. The retention of significant neuronal Na+ blockade in all types of semirigid conformers gives evidence for a multiple mode of binding in this class of compounds and can possibly be attributed to a poor structural specificity of the site(s) of action. Compound 9b was also found to be the most active compound in vivo based on the high level of inhibition of seizures exhibited in the DBA/2 mouse model. The pK(a) value of 9b indicates that 9b binds to the channel in its protonated form, and log D vs pH measurements suggest that ion-pair partitioning contributes to membrane transport. This compound stands out as an interesting lead for further development of neurotherapeutic agents.
• Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt
  作者：Xiangchao Xu、Yao Ai、Rongzhou Wang、Liping Liu、Jiazhi Yang、Feng Li

  DOI：10.1016/j.jcat.2020.12.016

  日期：2021.3

  Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically

  设计，合成了带有功能性2,2'-联苯并咪唑配体[（p- Cymene）Ru（BiBzImH 2）Cl] [Cl]的钌配合物，它是通过无受体合成喹啉的通用高效催化剂。碳酸盐存在下邻氨基苄醇与酮的脱氢偶联。证实了配体中的NH单元对于催化活性至关重要。还进行了该催化体系在生物活性分子的规模克合成中的应用。值得注意的是，这项研究展示了金属-配体双功能催化剂在无受体脱氢反应中的新潜力。