(R,S)-1-(phenylthio)-2-aminopropane hydrochloride | 56216-00-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R,S)-1-(phenylthio)-2-aminopropane hydrochloride
• 英文别名: (+/-)-1-(phenylthio)-2-propylamine hydrochloride；β-phenylsulfanyl-isopropylamine; hydrochloride；β-Phenylmercapto-isopropylamin; Hydrochlorid；1-(Phenylthio)propan-2-amine hydrochloride；1-phenylsulfanylpropan-2-amine;hydrochloride
• CAS: 56216-00-3
• 化学式: C₉H₁₃NS*ClH
• 分子量: 203.736
• InChiKey: VOPKQTUUTACBSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  154.5-156 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-氯苯氧基)甲基]环氧乙烷 、 (R,S)-1-(phenylthio)-2-aminopropane hydrochloride 在 三乙胺 作用下， 生成 1-(2-Chloro-phenoxy)-3-(1-methyl-2-phenylsulfanyl-ethylamino)-propan-2-ol
  参考文献：
  名称：

  β-肾上腺素能阻断剂。18.1-（芳氧基）-3-（芳硫基烷基氨基）丙-2-醇和1-取代的烷基硫氨基-3-（芳氧基）丙-2-醇。

  摘要：

  描述了1-（芳氧基）-3-（芳硫基烷基氨基）丙烷-2-醇和1-（烷基硫氨基）-和1-（芳烷基氨基）-3-（芳氧基）丙烷-2-醇的衍生物系列的合成。研究了这些化合物的β-肾上腺素受体阻滞特性以及对心脏β1受体的选择性作用。特别参考硫，亚砜和砜基团对β-肾上腺素受体阻断效能和选择性的影响，讨论了结构活性关系。

  DOI：

  10.1021/jm00206a010
• 作为产物：
  描述：

  N-<2-Phenylmercapto-1-methyl-aethyl>-acetamid 在 盐酸 作用下， 反应 6.0h， 生成 (R,S)-1-(phenylthio)-2-aminopropane hydrochloride
  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

文献信息

• SNAr or Sulfonylation? Chemoselective Amination of Halo(het)arene Sulfonyl Halides for Synthetic Applications and Ultralarge Compound Library Design
  作者：Vasyl Naumchyk、Vladyslav A. Andriashvili、Dmytro S. Radchenko、Dmytro Dudenko、Yurii S. Moroz、Andrey A. Tolmachev、Serhii Zhersh、Oleksandr O. Grygorenko

  DOI：10.1021/acs.joc.3c02636

  日期：2024.3.1

  The chemoselectivity of halo(het)arene sulfonyl halide aminations is studied thoroughly under parallel synthesis conditions, and the scope and limitations of the method are established. It is shown that SNAr-reactive sulfonyl halides typically undergo sulfonamide synthesis during the first step; the second amination is also possible provided that the SNAr-active center is sufficiently reactive. On

  在平行合成条件下深入研究了卤代（杂）芳烃磺酰卤胺化物的化学选择性，并确定了该方法的范围和局限性。结果表明， SN Ar反应性磺酰卤通常在第一步中进行磺酰胺合成；如果SN Ar活性中心具有足够的反应性，则第二次胺化也是可能的。相反，带有芳基化部分的磺酰氟在适当的控制下在后一个反应中心发生选择性转化。进一步的硫-氟化物交换（SuFEx）也是可能的，这对于某些磺酰卤类特别有价值。开发的两步并行双胺化方案提供了对 66.7 亿个化合物的合成可处理 REAL 型化学空间的访问（预期合成成功率 76%）。
• Nair, M. D.; David, J.; Nagarajan, K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 940 - 947
  作者：Nair, M. D.、David, J.、Nagarajan, K.

  DOI：——

  日期：——
• Novelli; Zwaig, Anales des la Asociacion Quimica Argentina, 1944, vol. 32, p. 89,91
  作者：Novelli、Zwaig

  DOI：——

  日期：——
• 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：——
• NAIR M. D.; DAVID J.; NAGARAJAN K., INDIAN J. CHEM., 24,(1985) N 9, 940-947
  作者：NAIR M. D.、 DAVID J.、 NAGARAJAN K.

  DOI：——

  日期：——