(-)-(S)-N-[1-methyl-2-(phenylthio)ethyl]acetamide | 1252084-87-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (-)-(S)-N-[1-methyl-2-(phenylthio)ethyl]acetamide
• 英文别名: N-[(2S)-1-phenylsulfanylpropan-2-yl]acetamide
• CAS: 1252084-87-9
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: DCKGVDQXKBHNLI-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(S)-N-[1-methyl-2-(phenylthio)ethyl]acetamide 在 盐酸 作用下， 反应 6.0h， 生成 (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
• 作为产物：
  描述：

  苯硫酚 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 13.17h， 生成 (-)-(S)-N-[1-methyl-2-(phenylthio)ethyl]acetamide
  参考文献：
  名称：

  游离环丙基甲基胺的 Pd(II)-催化的对映选择性 γ-C(sp3)-H 官能化

  摘要：

  由于能够从简单而丰富的起始材料中可靠地锻造具有精确区域控制的立体中心，底物导向的对映选择性反应被广泛用于现代有机合成。因此，由先天官能团引导的对映选择性 C(sp3)-H 官能化反应可以提供在惰性烃部分中引入分子复杂性的新途径，但到目前为止，这种方法几乎没有成功。虽然游离的脂肪族伯胺是合成中常见的通用中间体，但它们在 C(sp3)-H 活化反应中通常不具有反应性。在此，我们报告了由手性二齿硫醚配体实现的游离脂肪胺（环丙基甲基胺）的 Pd 催化对映选择性 C(sp3)-H 功能化。这种配体' 特殊的双齿配位模式和硫醚基序有利于生成必需的单（胺）-Pd（II）中间体，从而使游离胺对映选择性 CH 活化。由此产生的 C-Pd(II) 物种可以参与 Pd(II)/Pd(IV) 或 Pd(II)/Pd(0) 催化循环，从而能够通过（杂）芳基化、羰基化获得多种产品和烯化反应。因此，这种多功能反应性为药

  DOI：

  10.1021/jacs.0c04801
• 作为试剂：
  描述：

  1-苄基环丙烷-1-羧酸 在 lithium hydroxide monohydrate 、 palladium diacetate 、 (-)-(S)-N-[1-methyl-2-(phenylthio)ethyl]acetamide 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 生成 dibenzyl (1S,2S)-1-benzylcyclopropane-1,2-dicarboxylate
  参考文献：
  名称：

  通过简单脂肪酸的配体启用 C-H 羰基化合成环状酸酐

  摘要：

  游离羧酸的 C(sp 3 )-H 官能化的发展提供了广泛的通用 C-C 和 C-Y（Y=杂原子）键形成反应。此外，C-H 官能化有助于一步制备许多有价值的合成基序，这些基序通常难以通过常规方法制备。在此，我们报道了使用 Mo(CO) 6对游离羧酸进行β- 或 γ-C(sp 3 )-H 羰基化作为一种方便的固体 CO 源并通过双齿配体实现，从而方便地合成环状酸酐。其中，琥珀酸酐产品是多用途的垫脚石，可通过脱羧官能化在母酸的 β 位单选择性引入各种官能团，从而提供了一种不同的策略来合成先前 β- 无法获得的大量羧酸。 C-H 活化反应。使用手性二齿硫醚配体还可以实现游离环丙烷羧酸的对映选择性羰基化

  DOI：

  10.1002/anie.202104645

文献信息

• Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
  作者：Alessia Carocci、Alessia Catalano、Angelo Lovece、Giovanni Lentini、Andrea Duranti、Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Carlo Franchini

  DOI：10.1016/j.bmc.2010.06.100

  日期：2010.9

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.
• Pd(II)-Catalyzed Enantioselective γ-C(sp³)–H Functionalizations of Free Cyclopropylmethylamines
  作者：Zhe Zhuang、Jin-Quan Yu

  DOI：10.1021/jacs.0c04801

  日期：2020.7.15

  widely used in modern organic synthesis. As such, enantioselective C(sp3)-H functionalization reactions directed by innate functional groups could provide new routes to introduce molecular complexity within the inert hydrocarbon moiety, but so far this approach has been met with little success. While free primary aliphatic amines are common, versatile intermediates in synthesis, they are traditionally unreactive

  由于能够从简单而丰富的起始材料中可靠地锻造具有精确区域控制的立体中心，底物导向的对映选择性反应被广泛用于现代有机合成。因此，由先天官能团引导的对映选择性 C(sp3)-H 官能化反应可以提供在惰性烃部分中引入分子复杂性的新途径，但到目前为止，这种方法几乎没有成功。虽然游离的脂肪族伯胺是合成中常见的通用中间体，但它们在 C(sp3)-H 活化反应中通常不具有反应性。在此，我们报告了由手性二齿硫醚配体实现的游离脂肪胺（环丙基甲基胺）的 Pd 催化对映选择性 C(sp3)-H 功能化。这种配体' 特殊的双齿配位模式和硫醚基序有利于生成必需的单（胺）-Pd（II）中间体，从而使游离胺对映选择性 CH 活化。由此产生的 C-Pd(II) 物种可以参与 Pd(II)/Pd(IV) 或 Pd(II)/Pd(0) 催化循环，从而能够通过（杂）芳基化、羰基化获得多种产品和烯化反应。因此，这种多功能反应性为药
• 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.