(S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether | 406945-07-1

• 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: (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether
• 英文别名: 3-[(2S)-2-phenyl-2-[4-(trifluoromethyl)phenoxy]ethyl]furan
• CAS: 406945-07-1
• 化学式: C₁₉H₁₅F₃O₂
• 分子量: 332.322
• InChiKey: FETXPVLMYUEMSM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether 在 N-甲基吗啉 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 硼烷 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.25h， 生成 (3S)-N-甲基-3-苯基-3-[4-(三氟甲基)苯氧基]-1-丙胺盐酸盐(1:1)
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride

  摘要：

  The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)(2)](4)/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)(2)](4)/(R)-BINOL was used in the first reaction to give the enantiomer of 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01012-2
• 作为产物：
  描述：

  3-糠醛 在 氢氧化钾 、 sodium hydride 、 肼 作用下， 以 N,N-二甲基乙酰胺 、 水 、 乙二醇 为溶剂， 反应 3.25h， 生成 (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride

  摘要：

  The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)(2)](4)/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)(2)](4)/(R)-BINOL was used in the first reaction to give the enantiomer of 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01012-2

文献信息

• Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride
  作者：William H Miles、Elizabeth J Fialcowitz、E Scott Halstead

  DOI：10.1016/s0040-4020(01)01012-2

  日期：2001.12

  The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)(2)](4)/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)(2)](4)/(R)-BINOL was used in the first reaction to give the enantiomer of 2. (C) 2001 Elsevier Science Ltd. All rights reserved.