tert-butyl[(3(R)-fluorohept-1-yn-7-yl)oxy]dimethyl silane | 915289-75-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl[(3(R)-fluorohept-1-yn-7-yl)oxy]dimethyl silane
• 英文别名: tert-butyl-[(5R)-5-fluorohept-6-ynoxy]-dimethylsilane
• CAS: 915289-75-7
• 化学式: C₁₃H₂₅FOSi
• 分子量: 244.425
• InChiKey: HKCZUBFJHGVDSH-LBPRGKRZSA-N

物化性质

• 沸点：
  257.2±30.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl[(3(R)-fluorohept-1-yn-7-yl)oxy]dimethyl silane 在 potassium fluoride 、 jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  7-(tert-butyldimethylsilanoxy)-1-heptyn-3S-ol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到tert-butyl[(3(R)-fluorohept-1-yn-7-yl)oxy]dimethyl silane
  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.