(2S)-<2-2H>-propiophenone | 135561-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-<2-2H>-propiophenone
• 英文别名: (2S)-2-deuterio-1-phenylpropan-1-one
• CAS: 135561-72-7
• 化学式: C₉H₁₀O
• 分子量: 135.17
• InChiKey: KRIOVPPHQSLHCZ-SKEHDUAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-<2-2H>-propiophenone 在 吡啶 、 sodium tetrahydroborate 、 phosphate buffer 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.5h， 生成 (1R,2S)-1-phenylpropan-2-d-1-ol
  参考文献：
  名称：

  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine

  摘要：

  Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-1-phenylpropan-1-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from alpha,alpha-dideuterio-3-chloropropiophenone (8) was shown to possess the 2S configuration 10 by conversion into [2-H-2]-(1R,2S)-1-phenylpropan-1-ol (13), whose stereochemistry was assigned by comparison of its NMR properties with those of the [2-H-2]-(1S,2S) diastereoisomer 19 synthesized from yeast-generated (1R,2S)-1-phenylpropane-1,2-diol (15). Whereas product 3 is converted into (R)-fluoxetine (31), 2S alcohol 24, obtained in the yeast reduction of the ketone 22 is transformed into (R)-fenfluramine (29) and into its enantiomer (26).

  DOI：

  10.1021/jo00021a011
• 作为产物：
  描述：

  ethyl benzoylacetate-d2 在 四氯化碳 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 91.0h， 生成 (2S)-<2-2H>-propiophenone
  参考文献：
  名称：

  The mode of bakers' yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H]propiophenone, (R)-fluoxetine, and (R)- and (S)-fenfluramine

  摘要：

  Yeast treatment of 3-chloropropiophenone (2) affords the expected (1S)-3-chloro-1-phenylpropan-1-ol (3) as well as ca. 30% of propiophenone (5). The conversion of 2 into 5 is accompanied by formal elimination of hydrochloric acid, followed by yeast saturation of the double bond of the intermediate phenyl vinyl ketone (4). Monodeuteriopropiophenone formed via yeast treatment from alpha,alpha-dideuterio-3-chloropropiophenone (8) was shown to possess the 2S configuration 10 by conversion into [2-H-2]-(1R,2S)-1-phenylpropan-1-ol (13), whose stereochemistry was assigned by comparison of its NMR properties with those of the [2-H-2]-(1S,2S) diastereoisomer 19 synthesized from yeast-generated (1R,2S)-1-phenylpropane-1,2-diol (15). Whereas product 3 is converted into (R)-fluoxetine (31), 2S alcohol 24, obtained in the yeast reduction of the ketone 22 is transformed into (R)-fenfluramine (29) and into its enantiomer (26).

  DOI：

  10.1021/jo00021a011