(R)-2,4-dimethyl-2-oxazoline | 131830-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (R)-2,4-dimethyl-2-oxazoline
• 英文别名: (R)-DMeOx；(R,S)-2,4-Dimethyl-4,5-dihydro-oxazole；(4R)-2,4-dimethyl-4,5-dihydro-1,3-oxazole
• CAS: 131830-48-3
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: BEQDKWKSUMQVMX-SCSAIBSYSA-N

物化性质

• 沸点：
  106.9±9.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2,4-dimethyl-2-oxazoline 、 苯硫酚 反应 6.0h， 生成 (+)-(R)-N-[1-methyl-2-(phenylthio)ethyl]acetamide
  参考文献：
  名称：

  The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analog for dopamine .beta.-monooxygenase

  摘要：

  We have found that (R,S)-1-(phenylthio)-2-aminopropane (4a), a synthetic alternate substrate for the terminal enzyme of norepinephrine biosynthesis, dopamine beta-monooxygenase (DBM), is both an indirect sympathomimetic and a potent antihypertensive agent in spontaneously hypertensive rats. We demonstrate herein that there is a distinct enantiospecific difference in the activities of (R)-1-(phenylthio)-2-aminopropane (4b) and (S)-1-(phenylthio)-2-aminopropane (4c). We find that 4c, the more potent DBM substrate analogue, exhibits both the indirect sympathomimetic activity and the antihypertensive activity previously observed for the racemate and inhibits the active transport of catecholamines at the nerve terminal. In contrast, 4b, which is less potent as a DBM substrate or as an inhibitor of catecholamine uptake, does not exhibit an indirect sympathomimetic effect and is not an effective antihypertensive agent. These results suggest that the greater selectivity of the S enantiomer for both the catecholamine reuptake transporter and the target enzyme DBM accounts for its greater potency as an indirect-acting sympathomimetic agent as well as its activity as an antihypertensive agent. These results are also consistent with the hypothesized mechanism of action of this class of sulfur-containing DBM substrate analogues.

  DOI：

  10.1021/jm00107a031
• 作为产物：
  描述：

  D-氨基丙醇 、 乙基乙酰亚胺盐酸盐 以 二氯甲烷 为溶剂， 反应 6.0h， 以55%的产率得到(R)-2,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  基于HPLC的方法，用于确定α-手性胺的绝对构型。

  摘要：

  我们介绍了一种新颖的，基于HPLC的方法来轻松确定α-手性胺的绝对构型。我们的方法可轻松应用于多种化合物，包括氨基酸衍生物。该方法包括用手性衍生试剂N-琥珀酰亚胺基α-甲氧基苯基乙酸酯（SMPA）对手性胺分析物进行初始衍生，以产生相应的非对映异构体加合物。检查SMPA加合物的特定旋转异构体并应用简单规则即可将绝对构型与HPLC洗脱顺序关联起来。我们方法的一个关键方面是它可以用于确定绝对构型，而无需使用胺分析物的对映体标准品。此外，最重要的是，即使仅存在一种绝对构型未知的分析物对映体，我们的方法也可用于确定绝对构型，如酶促产物，天然衍生的化合物或通过手性合成制备的对映体富集的化合物通常如此。我们已经观察到各种α-手性胺的预测构型和观察到的绝对构型之间严格遵守。我们在本文中介绍的色谱方法非常实用，与以前开发的基于NMR的方法相比，具有一些重要的优点。例如，复杂的酶混合物中分析物的微克量可以通过

  DOI：

  10.1021/ac00058a025

文献信息

• HERMAN, HEATH H.;HUSAIN, PHILIP A.;COLBERT, JAMES E.;SCHWERI, MARGARET M.+, J. MED. CHEM., 34,(1991) N, C. 1082-1085
  作者：HERMAN, HEATH H.、HUSAIN, PHILIP A.、COLBERT, JAMES E.、SCHWERI, MARGARET M.+

  DOI：——

  日期：——
• The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analog for dopamine .beta.-monooxygenase
  作者：Heath H. Herman、Philip A. Husain、James E. Colbert、Margaret M. Schweri、Stanley H. Pollock、Lydia C. Fowler、Sheldon W. May

  DOI：10.1021/jm00107a031

  日期：1991.3

  We have found that (R,S)-1-(phenylthio)-2-aminopropane (4a), a synthetic alternate substrate for the terminal enzyme of norepinephrine biosynthesis, dopamine beta-monooxygenase (DBM), is both an indirect sympathomimetic and a potent antihypertensive agent in spontaneously hypertensive rats. We demonstrate herein that there is a distinct enantiospecific difference in the activities of (R)-1-(phenylthio)-2-aminopropane (4b) and (S)-1-(phenylthio)-2-aminopropane (4c). We find that 4c, the more potent DBM substrate analogue, exhibits both the indirect sympathomimetic activity and the antihypertensive activity previously observed for the racemate and inhibits the active transport of catecholamines at the nerve terminal. In contrast, 4b, which is less potent as a DBM substrate or as an inhibitor of catecholamine uptake, does not exhibit an indirect sympathomimetic effect and is not an effective antihypertensive agent. These results suggest that the greater selectivity of the S enantiomer for both the catecholamine reuptake transporter and the target enzyme DBM accounts for its greater potency as an indirect-acting sympathomimetic agent as well as its activity as an antihypertensive agent. These results are also consistent with the hypothesized mechanism of action of this class of sulfur-containing DBM substrate analogues.
• HPLC-based method for determination of absolute configuration of .alpha.-chiral amines
  作者：Philip A. Husain、Jayanta. Debnath、Sheldon W. May

  DOI：10.1021/ac00058a025

  日期：1993.5.15

  rotomer of the SMPA adduct and application of simple rules correlates absolute configuration and HPLC elution order. A key aspect of our method is that it can be used to determine absolute configuration without using enantiomeric standards of the amine analytes. Furthermore, it is of utmost significance that our method can also be used to determine absolute configuration even when only one analyte enantiomer

  我们介绍了一种新颖的，基于HPLC的方法来轻松确定α-手性胺的绝对构型。我们的方法可轻松应用于多种化合物，包括氨基酸衍生物。该方法包括用手性衍生试剂N-琥珀酰亚胺基α-甲氧基苯基乙酸酯（SMPA）对手性胺分析物进行初始衍生，以产生相应的非对映异构体加合物。检查SMPA加合物的特定旋转异构体并应用简单规则即可将绝对构型与HPLC洗脱顺序关联起来。我们方法的一个关键方面是它可以用于确定绝对构型，而无需使用胺分析物的对映体标准品。此外，最重要的是，即使仅存在一种绝对构型未知的分析物对映体，我们的方法也可用于确定绝对构型，如酶促产物，天然衍生的化合物或通过手性合成制备的对映体富集的化合物通常如此。我们已经观察到各种α-手性胺的预测构型和观察到的绝对构型之间严格遵守。我们在本文中介绍的色谱方法非常实用，与以前开发的基于NMR的方法相比，具有一些重要的优点。例如，复杂的酶混合物中分析物的微克量可以通过