氨氯地平杂质62 | 130161-00-1

• 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
• 中文名称: 氨氯地平杂质62
• 英文名称: 3-O-ethyl 5-O-methyl 4-(2-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 130161-00-1
• 化学式: C₁₈H₁₈ClNO₄
• 分子量: 347.798
• InChiKey: DZKNREBSUBFVSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氨氯地平杂质48 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以100%的产率得到氨氯地平杂质62
  参考文献：
  名称：

  Rapid, High-Yield Oxidation of Hantzsch-Type 1,4-Dihydropyridines with Ceric Ammonium Nitrate

  摘要：

  使用两个当量的硝酸铈铵，4-芳基-2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸盐（汉茨奇型 1,4-二氢吡啶）可被快速氧化成相应的吡啶衍生物，产量极佳。

  DOI：

  10.1055/s-1990-26982

文献信息

• Phototransformation of Amlodipine: Degradation Kinetics and Identification of Its Photoproducts
  作者：Anna Jakimska、Magdalena Śliwka-Kaszyńska、Piotr Nagórski、Jacek Namieśnik、Agata Kot-Wasik

  DOI：10.1371/journal.pone.0109206

  日期：——

  Nowadays, monitoring focuses on the primary compounds and does not include degradation products formed during various biological and chemical processes. Transformation products may have the same effects to human health and the environment or sometimes they can be more toxic than the parent compound. Unfortunately, knowledge about the formation of degradation products is still limited, however, can be very important for the environmental risk assessment. Firstly, the photodegradation kinetic of amlodipine was investigated in two experimental conditions: during the exposure to solar radiation and during the exposure to the light emitted by the xenon lamp. In all cases degradation of amlodipine followed a pseudo-first-order kinetics. In the next step, identification of transformation products of amlodipine formed during the exposure to xenon lamp irradiation was performed using ultra high performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS). As a result sixteen photoproducts were identified, their structures were elucidated and ultimately the transformation pathway was proposed. Fifteen compounds (out of 16 photoproducts) were newly identified and reported here for the first time; some of those compounds were formed from the first photoproduct, amlodipine pyridine derivative. Several analytes were formed only in acidic or basic conditions. Furthermore, the occurrence of amlodipine and its identified degradation products was investigated in environmental waters. Only one out of 16 compounds was found in wastewater effluent. The possibility of the sorption of examined analytes to sewage sludge particles was discussed based on QSAR.

  如今，监测的重点是原生化合物，而不包括在各种生物和化学过程中形成的降解产物。降解产物可能对人类健康和环境产生相同的影响，有时甚至比母体化合物毒性更大。遗憾的是，有关降解产物形成的知识仍然有限，但这对环境风险评估却非常重要。首先，在两种实验条件下研究了氨氯地平的光降解动力学：暴露在太阳辐射下和暴露在氙灯发出的光下。在所有情况下，氨氯地平的降解都遵循假一阶动力学。下一步，使用超高效液相色谱-四极杆飞行时间质谱（UHPLC-QTOF-MS）对氙灯照射过程中形成的氨氯地平转化产物进行了鉴定。结果确定了 16 种光反应产物，阐明了它们的结构，并最终提出了转化途径。在 16 种光反应产物中，有 15 种化合物是新发现的，并在此首次报道；其中一些化合物是由第一种光反应产物氨氯地平吡啶衍生物形成的。有几种分析物仅在酸性或碱性条件下生成。此外，还调查了环境水体中氨氯地平及其降解产物的存在情况。在废水中只发现了 16 种化合物中的一种。在 QSAR 的基础上讨论了污水污泥颗粒吸附受检分析物的可能性。
• Enantioselective Catalytic Hantzsch Dihydropyridine Synthesis
  作者：Xinyue Hu、Long Chen、Hongye Li、Qifan Xu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acscatal.2c05888

  日期：2023.5.19

  obtained through the asymmetric catalytic cascade reaction between 3-amino-2-butenoates and (Z)-2-arylidene-3-oxobutanoates. The N,N′-dioxide/NiII or NdIII complex catalysts were disclosed to be efficient, furnishing a variety of the products, including drugs like nitrendipine, nimodipine, and felodipine, in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee). Two enantiomers

  通过 3-amino-2-butenoates 和 ( Z )-2-arylidene-3-oxobutanoates 之间的不对称催化级联反应，获得了带有不同酯基的光学富集的 Hantzsch 二氢吡啶。N ，N'-二氧化物/Ni II或 Nd III络合物催化剂据称是高效的，以高产率（高达 99% 的产率）和优异的性能提供多种产品，包括尼群地平、尼莫地平和非洛地平等药物对映选择性（高达 99% ee）。通过两种反应物酯基的交换，很容易得到产物的两种对映异构体。此外，还通过氧化过程提供了轴向手性 4-芳基吡啶。
• PFISTER, JURG R., SYNTHESIS,(1990) N, C. 689-690
  作者：PFISTER, JURG R.

  DOI：——

  日期：——
• Rapid, High-Yield Oxidation of Hantzsch-Type 1,4-Dihydropyridines with Ceric Ammonium Nitrate
  作者：Jürg R. Pfister

  DOI：10.1055/s-1990-26982

  日期：——

  4-Aryl-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylates, Hantzsch-type 1,4-dihydropyridines, are rapidly oxidized to the corresponding pyridine derivatives in excellent yields using two equivalents of ceric ammonium nitrate.

  使用两个当量的硝酸铈铵，4-芳基-2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸盐（汉茨奇型 1,4-二氢吡啶）可被快速氧化成相应的吡啶衍生物，产量极佳。