(S)-3-amino-1-thiophen-2-yl-propan-1-ol | 1045348-04-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-3-amino-1-thiophen-2-yl-propan-1-ol
• 英文别名: (1S)-3-amino-1-(thiophen-2-yl)propan-1-ol；(1S)-3-amino-1-thiophen-2-ylpropan-1-ol
• CAS: 1045348-04-6
• 化学式: C₇H₁₁NOS
• 分子量: 157.236
• InChiKey: OFOQLYYHEOJCSK-LURJTMIESA-N

物化性质

• 沸点：
  304.9±32.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-1-thiophen-2-yl-propan-1-ol 在 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 52.5h， 生成 度洛西汀
  参考文献：
  名称：

  通过硫代酰胺的直接催化不对称醛醇缩合反应对苯氧西汀的简单对映体选择性合成

  摘要：

  硫酰胺的直接催化不对称醛醇缩合反应为度洛西汀的简明对映选择性合成提供了新途径。LiAlH 4还原后，直接羟醛方案可扩展（> 20 g），以92％ee得到羟醛产物，重结晶后可回收84％的手性配体。转化的以下四个步骤提供了度洛西汀。

  DOI：

  10.1021/jo300566p
• 作为产物：
  描述：

  (S)-3-azido-1-(2-thienyl)-1-propanol 生成 (S)-3-amino-1-thiophen-2-yl-propan-1-ol
  参考文献：
  名称：

  Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification

  摘要：

  An enantioselective synthesis of chiral gamma-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing gamma-azidoalcohols in high enantiomeric excess. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.028

文献信息

• Polymer-supported chiral sulfonamide catalyzed one-pot reduction of β-keto nitriles: a practical synthesis of (R)-fluoxetine and (R)-duloxetine
  作者：Guangyin Wang、Xingshun Liu、Gang Zhao

  DOI：10.1016/j.tetasy.2005.04.002

  日期：2005.5

  Enantioselective reduction of β-keto nitriles to optically active 1,3-amino alcohols has been carried out in one step using an excess of borane–dimethyl sulfide complex as a reductant and a polymer-supported chiral sulfonamide as a catalyst with moderate to high enantioselectivity. The facile and enantioselective method to prepare optically active 1,3-amino alcohols to be converted into 3-aryloxy-

  使用过量的硼烷-二甲硫醚络合物作为还原剂和聚合物负载的手性磺酰胺作为中等至高对映选择性的催化剂，已一步一步将β-酮腈对映体还原为光学活性1,3-氨基醇。还报道了制备旋光的1，3-氨基醇以转化为3-芳氧基-3-芳基丙胺型抗抑郁药（R）-氟西汀和（R）-度洛西汀的简便且对映选择性的方法。
• A facile asymmetric synthesis of (S)-duloxetine
  作者：Kee-In Lee、Se Hun Kwak、Jung Min Seo

  DOI：10.3998/ark.5550190.0011.a05

  日期：——

  The asymmetric-transfer hydrogenation of 2-tosyloxy-1-(2-thiophenyl)ethanone and further elaboration of the cyclic carbamate derived from γ-aminoalcohol to provide a facile synthesis of (S)-duloxetine, a potent dual inhibitor of serotonin and norepinephrine reuptake, is described.

  2-tosyloxy-1-(2-thiophenyl)ethanone 的不对称转移氢化以及衍生自 γ-aminoalcohol 的环状氨基甲酸酯的进一步加工，以提供 (S)-duloxetine 的简便合成，一种有效的血清素和去甲肾上腺素双重抑制剂再摄取，描述。
• Inhibition of serotonin and norepinephrine reuptake and inhibition of phosphodiesterase by multi-target inhibitors as potential agents for depression
  作者：John R. Cashman、Senait Ghirmai

  DOI：10.1016/j.bmc.2009.08.025

  日期：2009.10

  Compounds possessing more than one functional activity incorporated into the same molecule may have advantages in treating complex disease states. Balanced serotonin/norepinephrine reuptake inhibitors (SNRIs) (i.e., (R)- and (S)-norduloxetine) were chemically linked to a PDE4 inhibitor via a five carbon bridge. The new dual SNRI/PDE4 inhibitors (i.e., (R)-15 and (S)-15) showed moderately potent serotonin reuptake inhibition (IC(50) values of 442 and 404 nM, respectively) but low reuptake inhibition of norepinephrine (IC(50) values of 2097 and 2190 nM, respectively) in vitro. The dual SNRI/PDE4 inhibitors (i.e., (R)-15 and (S)-15) also inhibited PDE4D2 (i.e., K(i) values of 23 and 45 nM, respectively). Due to their synergistic functional activity, SNRI/PDE4 inhibitors may be effective in treating diseases such as depression. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of duloxetine and its enantiomer: lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile
  作者：Ahmed Kamal、G.B.Ramesh Khanna、R Ramu、T Krishnaji

  DOI：10.1016/s0040-4039(03)00945-6

  日期：2003.6

  An efficient and facile chemoenzymatic synthesis of duloxetine by lipase mediated resolution of 3-hydroxy-3-(2-thienyl)propanenitrile has been achieved. This process also describes an en antioconvergent synthesis of duloxetine via a Mitsunobu reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.
• J. Org. Chem. 2012, 77, 4496-4500
  作者：

  DOI：——

  日期：——