4-甲基-2-苯基-2-吗啉醇 | 21837-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 4-甲基-2-苯基-2-吗啉醇
• 英文名称: 2-[(4-phenyl)phenyl]-4-methylmorpholin-2-ol
• 英文别名: 4-methyl-2-phenylmorpholin-2-ol；4-methyl-2-phenyl-morpholin-2-ol；2-Phenyl-2-hydroxy-4-methyl-morpholin；2-Hydroxy-2-phenyl-4-methylmorpholin；2-OH-2-PH-4-ME Morpholine (hcl)
• CAS: 21837-62-7
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: OZIXBYYNZARVQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-2-苯基-2-吗啉醇 在 氢溴酸 、 silver nitrate 作用下， 以 乙醚 、 丙酮 、 乙腈 为溶剂， 反应 2.0h， 生成 2-phenyl-2-(3-nitrooxypropoxy)-4-methylmorpholine
  参考文献：
  名称：

  Nitric Oxide Releasing Morpholine Derivatives as Hypolipidemic and Antioxidant Agents

  摘要：

  The synthesis and evaluation of activity of some nitric acid esters of substituted morpholines are presented. All compounds inhibit lipid peroxidation and reduce cholesterol (20-63%) and triglyceride (37-85%) plasma levels. The more potent NO donors 14 and 17 specifically reduce low-density lipoprotein (LDL). These data indicate that proper structural modifications to the hypolipidemic and antioxidant morpholines enabling NO production; besides preserving or enhancing the above activities, offer a remarkable reduction of LDL, considered advantageous for antiatheromatic agents.

  DOI：

  10.1021/jm011062i
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 2-溴苯乙酮 以 乙醚 为溶剂， 反应 24.0h， 以90%的产率得到4-甲基-2-苯基-2-吗啉醇
  参考文献：
  名称：

  Evaluation of [11C]hemicholinium-15 and [18F]hemicholinium-15 as new potential PET tracers for the high-affinity choline uptake system in the heart

  摘要：

  [C-11]Hemicholinium-15 ([C-11]HC-15) and [F-18]hemicholinium-15 ([F-18]HC-15) have been synthesized as new potential PET tracers for the heart high-affinity choline uptake (HACU) system. [C-11]HC-15 was prepared by N-[C-11]methylation of the appropriate precursor, 4-methyl-2-phenyl-morpholin-2-ol, using [C-11]CH3OTf in 55-70% radiochemical yield decay corrected to end of bombardment (EOB) and 2-3 Ci/mu mol specific activity at end of synthesis (EOS). [F-18]HC-15 was prepared by N-[F-18]fluoromethylation of the precursor using [F-18]FCH2OTf in 20-30% radiochemical yield decay corrected to EOB and > 1.0 Ci/mu mol specific activity at EOS. The biodistribution of both compounds was determined in rats at 20 min post-intravenous injection, and the results show the heart region uptakes 1.32 +/- 0.75%ID/g in R-ventricle for [C-11]HC-15 and 1.28 +/- 0.81%ID/g in L-ventricle for [F-18]HC-15, respectively. The dynamic PET imaging studies of [C-11]HC-15 in rats were acquired 60 min post-intravenous injection of the tracer using the IndyPET-II scanner. For the blocking experiments, the rats were intravenously pretreated with 3.0 mg/kg of unlabeled HC-15 prior to [C-11]HC-15 injection. [C-11]HC-15 rat heart PET studies show rapid heart uptake to give clear heart images. The rat heart PET blocking studies found no significant blocking effect. The dynamic PET studies in normal and ablated dogs were performed using Siemens PET scanner with [N-13]NH3, [C-11]HC-15, and [F-18]HC-15. PET studies in dogs of both [C-11]HC-15 and[F-18]HC-15 also show significant heart uptake and give images of the heart. However, there is no significant change in [C-11]HC-15 L-ventricle uptake following radiofrequency ablation in the dog. These results suggest that the localization of HC-15 tracers in the heart is mediated by non-specific processes, and the visualization of HC-15 tracers on the heart is related to non-specific binding of HACU. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.014

文献信息

• Thiomorpholine Derivatives with Hypolipidemic and Antioxidant Activity
  作者：Kyriaki-Konstantina Tooulia、Panagiotis Theodosis-Nobelos、Eleni A. Rekka

  DOI：10.1002/ardp.201500147

  日期：2015.9

  A number of thiomorpholine derivatives that are structurally similar to some substituted morpholines possessing antioxidant and hypocholesterolemic activity were synthesized. The new compounds incorporate an antioxidant moiety as the thiomorpholine N‐substituent. The derivatives were found to inhibit the ferrous/ascorbate‐induced lipid peroxidation of microsomal membrane lipids, with IC50 values as

  合成了许多结构上类似于一些具有抗氧化和降胆固醇活性的取代的吗啉的硫代吗啉衍生物。新化合物包含抗氧化部分作为硫代吗啉 N 取代基。发现这些衍生物抑制亚铁/抗坏血酸诱导的微粒体膜脂质脂质过氧化，IC5​​0 值低至 7.5 µM。此外，这些化合物表现出降低胆固醇和降低血脂的作用。活性最强的化合物 (5) 在 56 mmol/kg 时使 Triton WR-1339 诱导的高脂血症大鼠血浆中的甘油三酯、总胆固醇和低密度脂蛋白水平分别降低 80%、78% 和 76%。 ip）。它们还可以作为角鲨烯合酶抑制剂。
• Evaluation of [11C]hemicholinium-15 and [18F]hemicholinium-15 as new potential PET tracers for the high-affinity choline uptake system in the heart
  作者：Mingzhang Gao、Michael A. Miller、Timothy R. DeGrado、Bruce H. Mock、John C. Lopshire、Joshua G. Rosenberger、Cristian Dusa、Mithilesh Kumar Das、William J. Groh、Douglas P. Zipes

  DOI：10.1016/j.bmc.2006.11.014

  日期：2007.2.1

  [C-11]Hemicholinium-15 ([C-11]HC-15) and [F-18]hemicholinium-15 ([F-18]HC-15) have been synthesized as new potential PET tracers for the heart high-affinity choline uptake (HACU) system. [C-11]HC-15 was prepared by N-[C-11]methylation of the appropriate precursor, 4-methyl-2-phenyl-morpholin-2-ol, using [C-11]CH3OTf in 55-70% radiochemical yield decay corrected to end of bombardment (EOB) and 2-3 Ci/mu mol specific activity at end of synthesis (EOS). [F-18]HC-15 was prepared by N-[F-18]fluoromethylation of the precursor using [F-18]FCH2OTf in 20-30% radiochemical yield decay corrected to EOB and > 1.0 Ci/mu mol specific activity at EOS. The biodistribution of both compounds was determined in rats at 20 min post-intravenous injection, and the results show the heart region uptakes 1.32 +/- 0.75%ID/g in R-ventricle for [C-11]HC-15 and 1.28 +/- 0.81%ID/g in L-ventricle for [F-18]HC-15, respectively. The dynamic PET imaging studies of [C-11]HC-15 in rats were acquired 60 min post-intravenous injection of the tracer using the IndyPET-II scanner. For the blocking experiments, the rats were intravenously pretreated with 3.0 mg/kg of unlabeled HC-15 prior to [C-11]HC-15 injection. [C-11]HC-15 rat heart PET studies show rapid heart uptake to give clear heart images. The rat heart PET blocking studies found no significant blocking effect. The dynamic PET studies in normal and ablated dogs were performed using Siemens PET scanner with [N-13]NH3, [C-11]HC-15, and [F-18]HC-15. PET studies in dogs of both [C-11]HC-15 and[F-18]HC-15 also show significant heart uptake and give images of the heart. However, there is no significant change in [C-11]HC-15 L-ventricle uptake following radiofrequency ablation in the dog. These results suggest that the localization of HC-15 tracers in the heart is mediated by non-specific processes, and the visualization of HC-15 tracers on the heart is related to non-specific binding of HACU. (c) 2006 Elsevier Ltd. All rights reserved.
• Nitric Oxide Releasing Morpholine Derivatives as Hypolipidemic and Antioxidant Agents
  作者：Michael C. Chrysselis、Eleni A. Rekka、Ioanna C. Siskou、Panos N. Kourounakis

  DOI：10.1021/jm011062i

  日期：2002.11.1

  The synthesis and evaluation of activity of some nitric acid esters of substituted morpholines are presented. All compounds inhibit lipid peroxidation and reduce cholesterol (20-63%) and triglyceride (37-85%) plasma levels. The more potent NO donors 14 and 17 specifically reduce low-density lipoprotein (LDL). These data indicate that proper structural modifications to the hypolipidemic and antioxidant morpholines enabling NO production; besides preserving or enhancing the above activities, offer a remarkable reduction of LDL, considered advantageous for antiatheromatic agents.