(5R)-5-fluorohept-6-ynoic acid | 915289-77-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R)-5-fluorohept-6-ynoic acid
• CAS: 915289-77-9
• 化学式: C₇H₉FO₂
• 分子量: 144.146
• InChiKey: XTDHIKRGMHGRHM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-5-fluorohept-6-ynoic acid 、 甲醇 在 Amberlyst 15 作用下， 反应 24.0h， 以0.08 g的产率得到methyl 5-(R)-fluorohept-6-ynoate
  参考文献：
  名称：

  Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

  摘要：

  The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's > 95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.010
• 作为产物：
  描述：

  7-[(tert-butyldimethylsilyl)oxy]-1-(trimethylsilyl)hept-1-yn-3-ol 在 Noyori's catalyst potassium fluoride 、 jones reagent 、 二乙胺基三氟化硫 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 异丙醇 、 丙酮 为溶剂， 反应 35.0h， 生成 (5R)-5-fluorohept-6-ynoic acid
  参考文献：
  名称：

  Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

  摘要：

  The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's > 95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.010

文献信息

• Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate
  作者：Vijaya Lingam Manthati、A. Sai Krishna Murthy、Frédéric Caijo、Delphine Drouin、Philippe Lesot、Danielle Grée、René Grée

  DOI：10.1016/j.tetasy.2006.08.010

  日期：2006.9

  The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's > 95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules. (c) 2006 Elsevier Ltd. All rights reserved.