(R)-2-azido-1-<3-(trifluoromethyl)phenyl>propane | 135561-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-azido-1-<3-(trifluoromethyl)phenyl>propane
• 英文别名: 1-[(2R)-2-azidopropyl]-3-(trifluoromethyl)benzene
• CAS: 135561-77-2
• 化学式: C₁₀H₁₀F₃N₃
• 分子量: 229.205
• InChiKey: KHKJZHWJPLFQLB-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-2-azido-1-<3-(trifluoromethyl)phenyl>propane 在 Lindlar's catalyst 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以67%的产率得到(R)-1-(3-三氟甲基苯基)-2-氨基丙烷
  参考文献：
  名称：

  Goument, B.; Duhamel, L.; Mauge, R., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 450 - 458

  摘要：

  DOI：
• 作为产物：
  描述：

  3-三氟甲基苯丙酮 在 吡啶 、 sodium azide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (R)-2-azido-1-<3-(trifluoromethyl)phenyl>propane
  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

文献信息

• Goument, B.; Duhamel, L.; Mauge, R., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 450 - 458
  作者：Goument, B.、Duhamel, L.、Mauge, R.

  DOI：——

  日期：——
• 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
  作者：Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Andrea Mele

  DOI：10.1021/jo00021a011

  日期：1991.10

  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).